Herbicidal diazoles

ABSTRACT

Certain diazole derivatives are useful as plant growth regulants and as herbicides.

RELATED APPLICATION

This application is a divisional application of U.S. Ser. No. 486,092 filed Apr. 25, 1983 which is under prosecution which is a continuation-in-part of U.S. Ser. No. 384,043 filed Jun. 1, 1982 which is abandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel diazoles, to herbicidal compositions containing them and to the method of using them for controlling the growth of undesired vegetation.

The control of undesired vegetation is desired in many instances. In the most common situation, it is desired to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such useful crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around fuel storage tanks, ammunition depots and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

U.S. Pat. No. 4,127,405, issued to Levitt on Nov. 28, 1978, discloses herbicidal sulfonamides of the formula ##STR1## where R₁ is selected from ##STR2## and where W and Q are independently O or S.

U.S. Pat. No. 4,169,719, issued to Levitt on Oct. 2, 1979, discloses pyrimidine compounds corresponding to the triazines disclosed in the '405 patent.

European Patent Application 81301874.4, published on Nov. 4, 1981, discloses herbicidal pyrrole sulfonamides of the formulas ##STR3## where R₁₀ is selected from ##STR4##

European Patent Application 80304287.8, published on Jun. 10, 1981, discloses herbicidal compounds of the formulas ##STR5## where W is O or S;

B is ##STR6## R₁ is ##STR7##

European Patent Application 81302461.9, published on Dec. 9, 1981, discloses herbicidal thiophenesulfonamides of the formula ##STR8## where R₅ is selected from ##STR9##

Nowhere in the art is there any indication that N-[(heterocyclic)aminocarbonyl]diazole sulfonamides could be prepared or that they would possess herbicidal utility.

SUMMARY OF THE INVENTION

It has now been found that the compounds of Formula I have utility as plant growth regulants and/or herbicides. ##STR10## where R is H or CH₃ ;

Q is ##STR11## R₁ is H, C₁ -C₈ alkyl, C₃ -C₆ alkenyl, C₅ -C₆ cycloalkyl, C₅ -C₆ cycloalkenyl, C₃ -C₆ alkynyl, C₄ -C₇ cycloalkylalkyl, (R₁₇ CH)_(n) C(O)R₁₆, (R₁₇ CH)_(n) CO₂ R₁₈, (R₁₇ CH)_(n) COSR₁₉, (R₁₇ CH)_(n) CONR₂₀ R₂₁, (R₁₇ CH)_(n) SO₂ NR₂₀ R₂₁, (R₁₇ CH)_(n) SO₂ R₂₂, ##STR12## or C₁ -C₆ alkyl substituted either with (a) 1-3 atoms of F, Br or Cl; or

(b) OR₁₆ ;

provided that,

(1) the total number of carbon atoms in R₁ is less than or equal to 8; and

(2) if R₁ is other than C₁ -C₃ alkyl, then R₃ must be H;

R₂, R₃ and R₄ are independently H or CH₃ ;

R₅ is H, C₁ -C₄ alkyl, --OR₆, NO₂, F, Cl, Br, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ;

R₆ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl C₃ -C₄ alkynyl, CO₂ R₁₈, SO₂ NR₂₀ R₂₁, SO₂ R₂₂ or C₁ -C₄ alkyl substituted with (a) 1-3 carbon atoms of F, Cl or Br; or (b) OCH₃ ;

provided that,

(1) when R₅ is other than H, CH₃, OCH₃ or NO₂, then R₆ is H or CH₃ ; and

(2) when R₆ is CO₂ R₁₈, SO₂ NR₂₀ R₂₁ or SO₂ R₂₂, then R₅ is H, CH₃, OCH₃ or NO₂ ;

R₇ is H or CH₃ ;

R₈ is H, C₁ -C₄ alkyl, --OR₁₆, NO₂, F, Cl, Br, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ;

R₉ is CH₃ or C₂ H₅ ;

R₁₀ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CO₂ R₂₄, SO₂ NR₂₀ R₂₁ or SO₂ R₂₂ ;

R₁₁ is H, C₁ -C₃ alkyl, F, Cl, Br, NO₂, --OR₁₆, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ; provided that, when R₁₀ is other than C₁ -C₃ alkyl, then R₁₁ is H, Cl, OCH₃, NO₂ or CH₃ ;

R₁₂ is H or CH₃ ;

R₁₃ and R₁₄ are independently H, C₁ -C₃ alkyl --OR₁₆, F, Cl, Br, NO₂, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ; provided that, when either of R₁₃ or R₁₄ is CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁, then the other is H, Cl, CH₃, OCH₃ or NO₂ ;

R₁₅ is H or CH₃ ;

R₁₆ is C₁ -C₃ alkyl;

R₁₇ is H or CH₃ ;

R₁₈ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ;

R₁₉ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl or CH₂ CH₂ OCH₃ ;

R₂₀ and R₂₁ are independently CH₃ or C₂ H₅ ;

R₂₂ is C₁ -C₃ alkyl or CF₃ ;

R₂₃ is H, Cl, Br, CH₃, F, CF₃, OCH₃ or NO₂ ;

R₂₄ is C₁ -C₃ alkyl or allyl;

R₂₅ is C₁ -C₃ alkyl;

m is 0, 1 or 2;

n is 0 or 1;

A is ##STR13## X is CH₃, OCH₃, Cl, F, OCF₂ H or SCF₂ H; Y is CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, CH(OCH₃)₂, OCH₂ CF₃, OCF₃, NH₂, NHCH₃, N(CH₃)₂ or GCF₂ T where G is O or S and T is H, CHClF, CHBrF, CF₂ H or CHFCF₃ ;

Z is CH or N;

Y₁ is H, Cl, CH₃, OCH₃ or OCF₂ H;

X₂ is OCH₃, CH₃, CH₂ CH₃, OCH₂ CH₃, SCH₃ or SCH₂ CH₃ ;

Y₂ is CH₃, CH₂ CH₃ or CH₂ CF₃ ;

X₃ is OCH₃ or CH₃ ;

provided that, when X is Cl or F, then Z is CH and Y is OCH₃, NH₂, NHCH₃ or N(CH₃)₂ ; and agriculturally suitable salts thereof.

This invention therefore relates to compounds of Formula I, to herbicidal compositions containing the compounds and to methods of using the compounds to control the growth of undesired vegetation.

Certain groups of compounds are preferred because of their high herbicidal and/or plant growth regulant activity and/or because of the ease with which they may be prepared. These preferred groups are as follows:

1. Compounds of Formula I where Q is Q-1 and R is H.

1a. Compounds of Preferred 1 where A is A-1, and Z is CH.

1b. Compounds of Preferred 1a where X is CH₃, Cl, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.

1c. Compounds of Preferred 1b where R₁ is H or C₁ -C₄ alkyl, and R₃ is H.

2. Compounds of Formula I where Q is Q-2, and R is H.

2a. Compounds of Preferred 2 where A is A-1, Z is CH and R₄ is H.

2b. Compounds of Preferred 2a where X is CH₃, Cl, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.

2c. Compounds of Preferred 2b where R₅ is H, CH₃, OCH₃, Cl, NO₂, CO₂ R₂₄ or SO₂ NR₂₀ R₂₁ and R₆ is H or C₁ -C₄ alkyl.

3. Compounds of Formula I where Q is Q-3 and R is H.

3a. Compounds of Preferred 3 where A is A-1, Z is CH and R₇ is H.

3b. Compounds of Preferred 3a where X is CH₃, Cl, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.

3c. Compounds of Preferred 3b where R₈ is Br, C₁ -C₄ alkyl, OCH₃, Cl, NO₂, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁.

4. Compounds of Formula I where Q is Q-4 and R is H.

4a. Compounds of Preferred 4 where A is A-1 and Z is CH.

4b. Compounds of Preferred 4a where X is CH₃, Cl, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.

4c. Compounds of Preferred 4b where R₁₀ is H, C₁ -C₃ alkyl, CO₂ CH₃, SO₂ CH₃ or SO₂ N(CH₃)₂ and R₁₁ is H, CH₃, OCH₃, Cl, Br, NO₂, CO₂ CH₃, SO₂ CH₃ or SO₂ N(CH₃)₂.

5. Compounds of Formula I where Q is Q-5 and R is H.

5a. Compounds of Preferred 5 where A is A-1 and Z is CH.

5b. Compounds of Preferred 5a where X is CH₃, Cl, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.

5c. Compounds of Preferred 5b where R₁₁ is H, CH₃, OCH₃, Cl, Br, NO₂, CO₂ CH₃, SO₂ CH₃ or SO₂ N(CH₃)₂.

6. Compounds of Formula I where Q is Q-6 and R is H.

6a. Compounds of Preferred 6 where A is A-1 and Z is CH.

6b. Compounds of Preferred 6a where X is CH₃, Cl, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.

6c. Compounds of Preferred 6b where R₁₃ and R₁₄ are independently H, CH₃, OCH₃, Cl, Br, NO₂, CO₂ CH₃, SO₂ CH₃ or SO₂ N(CH₃)₂.

The following compounds are specifically preferred because of their high herbicidal and/or plant growth regulant activity and/or because of the ease with which they may be synthesized.

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-(1-methylethyl)-1H-imidazole-2-sulfonamide, m.p. 185°-186° C.(d);

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-(1-methylethyl)-1H-imidazole-2-sulfonamide, m.p. 157°-158° C.(d);

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-(1-methylethyl)-1H-imidazole-2-sulfonamide, m.p. 166°-167° C.;

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-ethyl-1H-imidazole-2-sulfonamide, m.p. 196°-197° C.;

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-ethyl-1H-imidazole-2-sulfonamide, m.p. 178°-179° C.(d);

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-ethyl-1H-imidazole-2-sulfonamide, m.p. 186°-187° C.; and

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-5-bromo-1-methyl-1H-imidazole-4-sulfonamide, m.p. 205°-206° C.

DETAILED DESCRIPTION OF THE INVENTION Synthesis a. Compounds of the Invention

The diazolesulfonylureas of this invention can be prepared by a number of methods. These methods, and the publications or sources describing them, are as follows: ##STR14##

As shown in Equation 1, an appropriately substituted sulfonyl isocyanate (a) is reacted with an appropriate aminoheterocycle (b). The reaction is best carried out in an inert aprotic solvent, such as methylene chloride, tetrahydrofuran, acetonitrile, ether or chloroform, at temperatures ranging from about -20° to 50° C. In some cases, the desired product may crystallize from the reaction medium and may be filtered. Reaction products which are soluble in the reaction medium may be isolated by evaporation of the solvent, trituration of the residue with solvents such as diethyl ether, ethyl acetate, 1-chlorobutane or hexane. Chromatography (e.g., silica gel) may also be necessary for purification. This process is described in U.S. Pat. Nos. 4,127,405, 4,257,802 and 4,221,585. ##STR15##

As shown in Equation 2, compounds of Formula (I) can also be prepared by reacting a sulfonamide (e) with an appropriate methyl carbamate (d) in the presence of an equimolar amount of trimethylaluminum. The reaction is best run in an inert aprotic solvent such as methylene chloride at about 25° to 40° C. for 10 to 96 hours under a nitrogen atmosphere. The product can be isolated by addition of an aqueous acetic acid solution followed by extraction of the product into methylene chloride, or by filtration of a product of low solubility. The product can be purified by trituration with solvents such as 1-chlorobutane, ethyl acetate or ethyl ether or by column chromatography on silica gel. ##STR16##

Examples of other methods for preparing compounds of this invention are illustrated in Equations 3 and 4 and described in European Patent Application 80304285.2, published Jun. 10, 1981. The first step of this two-step process (Equation 3) involves reaction of a diazole sulfonamide and a heterocyclic isocyanate to yield an N-(haloheterocyclicaminocarbonyl)aromatic sulfonamide (f). This reaction is best run in an inert organic solvent such as acetonitrile, tetrahydrofuran, toluene, acetone or butanone, preferably at a temperature of about 25° to 110° C. The product can then be further reacted with selected nucleophiles, for example alkoxide --OR', (Equation 4) to yield herbicidal N-(substituted heterocyclicaminocarbonyl)aromatic sulfonamides of this invention. ##STR17## European Patent Application 81810282.4, published Jan. 27, 1982 ##STR18## European Patent Application 81810282.4, published Jan. 27, 1982

Equations 5 and 6 illustrate two additional methods for preparing the compounds of this invention. As shown in Equation 5, a diazole sulfonamide (e) is reacted with an N-heterocyclic carbamate (g) in the presence of a base. Alternatively, in Equation 6, an N-phenylsulfonylcarbamate (h) is reacted with an amine (b). Both of these processes are described in European Patent Application No. 81810281.6 (Publication No. 44,807, Jan. 27, 1982). Both reactions are best carried out in aprotic, inert organic solvents such as methylene chloride, tetrahydrofuran, acetonitrile, dioxane and toluene, at temperatures between -20° and 120° C. Suitable bases for use in the process of Equation 5 are organic bases such as amines and inorganic bases such as hydrides, hydroxides, carbonates and bicarbonates.

Compounds of Formula I in which Q is Q-1, R₁ is as defined above except that n must be 1, and R, R₂, R₃ and A are as defined previously, are best prepared by the procedures outlined in Equations 2, 5 or 6.

Compounds of Formula I in which Q is Q-2, Q-3, Q-4, Q-5 or Q-6, m is 0 or 2 and all other substituents are as previously defined are best prepared by the procedures of Equations 2, 5 or 6. Many of these compounds may also be prepared by the procedure of Equation 1. When m is 1, the compounds can be prepared by oxidation of the corresponding sulfide (m=0) with m-chloroperbenzoic acid as described in European Patent Application 81300956.0, published Sept. 16, 1981.

Compounds of this invention represented below by Formula 4 (Q of Formula I is Q-1, R₁ is (R₁₇ CH)_(n) COR₁₆, (R₁₇ CH)_(n) CO₂ R₁₈, (R₁₇ CH)_(n) COSR₁₉, (R₁₇ CH)_(n) CONR₂₀ R₂₁, (R₁₇ CH)_(n) SO₂ NR₂₀ R₂₁, or (R₁₇ CH)SO₂ R₂₂, and R, R₂, R₃ and A are as previously defined) may be prepared by the procedures outlined in Equations 7 or 8. ##STR19##

In both Equations 7 and 8, X_(a) can be Cl, Br or I and, when n is 0 and R₁ is C(O)R₁₆, then X_(a) can also be --OCOR₁₆, and when n is 0 and R₁ is --SO₂ R₂₂, then X_(a) can also be --OSO₂ R₂₂.

In Equation 7, a sulfonylurea 1 is reacted with an appropriate alkylating or acylating agent, R₁ X_(a), in a suitable solvent such as CH₂ Cl₂, xylene or tetrahydrofuran, for periods of 1 to 50 days at temperatures from ambient to the reflux temperature of the solvent. The salt 3 is neutralized to the product 4 by pouring the reaction mixture into water and reacting it with an appropriate amount of a base such as NaHCO₃ or Na₂ CO₃. The product is isolated by extraction and then purified by the usual techniques of crystallization or chromatography.

In Equation 8, the sulfonylurea 1 is converted to its dianion 5 with two equivalents of a strong base such as NaH, sec-butyllithium or potassium tert-butoxide, in a suitable solvent such as tetrahydrofuran. The dianion is treated with an equivalent of an alkylating or acylating agent, R₁ X_(a), to yield the salt of 4. The reaction mixture is poured into water and acidified to pH 2-3 with a mineral acid such as aqueous hydrochloric acid. The product 4 is isolated and purified as described for Equation 7.

b. Intermediate Compounds

Heterocyclic amines of formula (b) are known in the art. For procedures of synthesis see U.S. Pat. No. 4,127,405, U.S. Pat. No. 4,221,585, EP 0015683 and European Patent Application 81303837.9, published Mar. 3, 1982 and South African Patent Application 82/5045.

Heterocyclic carbamates of Formula (d) are prepared by procedures taught in U.S.S.N. 337,934, filed Jan. 7, 1982.

Sulfonyl isocyanates may be prepared by procedures taught in U.S. Pat. No. 4,127,405 and European Patent Application 80301848.0, published Jan. 7, 1981.

Sulfonamides of Formula (c) in which Q is Q-1, R₂ and R₃ are as previously defined, and R₁ is H, C₁ -C₈ alkyl; C₄ -C₇ cycloalkylalkyl, C₁ -C₆ alkyl substituted with 1-3 atoms of F, Br or Cl or with one --OR₁₆ ; or ##STR20## are prepared by procedures known in the art and also outlined in Equations 9, 10 and 10a. ##STR21##

Mercapto imidazoles 9 are known in the art. For representative procedures see R. G. Jones, E. C. Kornfeld, K. C. McLaughlin and R. C. Anderson, J. Am. Chem. Soc., 71 4000 (1949) and references cited therein.

The procedure for converting mercapto imidazoles 9 to sulfonamides (c-1), shown in Equation 10, is known in the art. Details can be found in R. O. Roblin, Jr. and James W. Clapp, J. Am. Chem. Soc., 72 4890 (1950). Improved yields of sulfonamides are sometimes obtained when stoichiometric quantities of Cl₂ are used in this procedure, rather than an excess as described.

Compounds of Formula (c) in which Q is Q-1, R₂ and R₃ are as previously defined, and R₁ is C₃ -C₆ alkenyl, C₃ -C₆ alkynyl, COR₁₆, CO₂ R₁₈, COSR₁₉, CONR₂₀ R₂₁, SO₂ NR₂₀ R₂₁ or SO₂ R₂₂ are best prepared by the procedure of Equation 11. ##STR22## X_(a) is Cl or Br; when R₁ is C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, X_(a) can also be I;

when R₁ is COR₁₆, X_(a) can also be OCOR₁₆, and

when R₁ is SO₂ R₂₂, X_(a) can also be OSO₂ R₂₂.

This method is known to those skilled in the art and is carried out in a manner analogous to the process outlined in Equation 7.

Many of the sulfonamides of Formula (c) are known in the art or can be prepared from known imidazole intermediates by chemical transformations known to those skilled in the art. General literature references describing the chemistry of imidazoles include:

Elderfield, Chemistry of Heterocyclic Compounds, Vol. V, p. 194-297, 1957, John Wiley and Sons, Inc., New York.

T. Kauffman and R. Werthwein, Angew Chem., Int. Ed. Engl. 10 20-33 (1971).

M. R. Grimmett, Adv. Heterocycl. Chem. 12. 104-184 (1970).

The preparation of substituted nitro imidazolesulfonamides of Formulas (c-3) and (c-4) (Q is Q-2 or Q-3 and R₅ and R₈ are --NO₂) is shown in Equation 12. ##STR23## where R₄ and R₇ are H;

R₆ and R₉ are H, CH₃ or CH₂ C₆ H₅ ;

X_(a) is Cl, Br or I; and

R₉ is CH₃ or CH₃ CH₂.

This process is as described in B. S. Huang, M. J. Lauzon and J. C. Parham, J. Het. Chem. 16, 811 (1979). Using similar procedures compounds of structure (c-3) in which R₉ is CH₃ CH₂, and R₇ is H or CH₃ can be prepared. Also, intermediates of structure (c-4) in which R₄ is CH₃ or H and R₆ is C₂ -C₄ alkyl; C₃ -C₄ alkenyl; C₁ -C₄ alkyl substituted with 1-3 atoms of F, Cl, Br or with OCH₃ ; CO₂ R₁₈ ; SO₂ NR₁₉ R₂₀ ; or SO₂ R₂₁ can be prepared.

The preparation of bromo or chloro imidazole sulfonamides of formula (c-5) and (c-6) (Q is Q-2 or Q-3 and R₅ and R₈ are Br or Cl) is outlined in Equation 12a. ##STR24##

The preparation of 4(5)bromo imidazole 16 is described by I. E. Balaban and F. L. Pyman, J. Chem. Soc., 121 947 (1922). The preparation of the 4(5)bromo-5(4)sulfonamide imidazole 17 is taught in L. L. Bennett and H. T. Baker, J. Am. Chem. Soc., 79, 2188 (1956).

The preparation of additional intermediates for use in preparing the compounds of this invention from readily available imidazole intermediates is outlined in Scheme 1. ##STR25##

The preparation of 4-chloro or bromo-5-nitroimidazole 18 is accomplished by procedures taught in I. E. Balaban and F. L. Pyman, J. Chem. Soc., 121 947 (1922).

Protection of the imidazole nitrogen for further manipulation of the ring is accomplished with such groups as CH₃ OCH₂ -- or CH₃ OCH₂ CH₂ O--CH₂ --. These groups can be introduced and removed by procedures taught in C. Tang, D. Davalian, P. Huang, and R. Breslow, J. Am. Chem. Soc., 3918 (1978) and E. J. Corey, J. L. Cras and P. Ulrich, Tet. Let. 809 (1976).

Protection and deprotection can also be accomplished with groups such as ##STR26## by procedures taught in T. Brown, G. Shaw and G. Durant, J. C. S. Perkin I 2310, (1980).

Protection of the imidazole as shown in Scheme I leads to a mixture of isomers 19 and 20.

The mixture is used without separation of the isomers in the following steps, since deprotection of either isomer eventually leads to the same product 30.

Introduction of R₅ or R₈ as F can be accomplished by procedures taught in U.S. Pat. No. 4,069,262 in which fluoronitrobenzene is produced from chloronitrobenzene by displacement with KF and CsF as catalyst.

Replacement of halogen in 19 and 20 to produce 21 and 22 in which R₅ and R₈ are --S(C₁ -C₃ alkyl) is accomplished by displacement of halogen with the appropriate mercaptide salt as shown in Scheme 1. Details for displacement of halogen by mercaptides in halonitroimidazoles can be found in L. L. Bennett and H. T. Baker, J. Am. Chem. Soc., 79, 2188, (1957). See this same reference for methods of oxidizing nitroalkylthioimidazoles to nitroalkylsulfonylimidazoles of Formulas 21 and 22 in which R₅ and R₈ are --SO₂ (C₁ -C₃ alkyl).

Compounds of Formulas 21 and 22 in which R₅ and R₈ are --SO₂ NR₂₀ R₂₁ are produced by oxidative chlorination of the corresponding thiol or benzylmercaptide to the sulfonyl chloride. Treatment of the sulfonyl chloride with two equivalents of R₂₀ R₂₁ NH produces the desired intermediates. This procedure is outlined in Scheme 2. ##STR27##

Conditions for carrying out the transformations outlined in Scheme 2 are known in the art. For example, see M. H. Fisher, W. H. Nichlolson and R. S. Stuart, Can. J. Chem., 39, 501 (1961), R. O. Roblin and J. W. Clapp, J. Am. Chem. Soc., 72, 4890 (1950) and U.S. Pat. No. 4,310,346.

Compounds of Formula 21 and 22 in which R₅ and R₈ and OR₁₆ and R₁₆ is C₁ -C₃ alkyl are produced by displacement of halogen in 19 and 20 with the appropriate alkoxide. Suitable procedures for replacement of an activated halogen with alkoxide can be found in R. S. Kittila, "Dimethylformamide Chemical Uses", Chapter 15, E. I. du Pont de Nemours and Company, Wilmington, Del. 19898.

Reduction of nitroimidazoles (shown in Scheme 1) of Formulas 21 and 22 in which R₄, R₅, R₇ and R₈ are as defined for Formula I can be accomplished by treatment with Adam's platinum catalyst, hydrogen and ethanol at room temperature and atmospheric pressure. For details see M. H. Fisher, W. H. Nicholson and R. S. Stuart, Can. J. Chem., 39, 501 (1961). Other suitable procedures which employ Raney nickel catalyst are taught in L. Bennett, Jr. and H. T. Baker, J. Am. Chem. Soc., 79 2188 (1957). Stannous chloride may also be used. See Fieser and Fieser, "Reagents for Organic Synthesis", Vol. I, p. 1113, J. Wiley and Sons, Inc., New York (1967) for details and references.

Imidazoles of Formula 39 ##STR28## in which R₄ is H or CH₃ and R₅ is H or C₁ -C₄ alkyl are produced by nitration of the corresponding imidazole 40 ##STR29## using procedures well known in imidazole chemistry. For example, see V. K. Bhagwat and F. L. Pyman, J. Chem. Soc., 127, 1832 (1925).

Conversion of 39 into the sulfonamides 41 in which R₄ is H or CH₃ and R₅ is H or C₁ -C₄ alkyl is accomplished by procedures ##STR30## analagous to those outlined in Scheme 1.

Functionalization of 41 to produce sulfonamides 42 and 43 is outlined in Scheme 3. ##STR31## This procedure, carried out under typical conditions for alkylating or acylating nitrogen, produces the mixture of isomeric sulfonamides 42 and 43 in which R₆ and R₉ are as defined for Formula I. ##STR32## in which R₄ is H or CH₃ and R₂₃ is C₁ -C₃ alkyl or allyl and ○P is a suitable protecting group such as t-butyl or a glycosyl group such as ##STR33## are prepared from the corresponding amino compound by diazotization, followed by coupling with SO₂ and HCl in the presence of a copper catalyst. The sulfonyl chlorides produced are converted to the sulfonamides by treatment with ammonia solution. This procedure is outlined in Scheme 4. ##STR34##

Protected amino esters 45 and the subsequent diazotization to produce diazonium chlorides 46 is taught in T. Brown, G. Shaw and G. Durant in J. Chem. Soc., Perkin Trans. I, 2304 (1980). The reaction of diazonium chlorides to produce sulfonamides is also outlined in Schemes 1 and 2. See the pertinent references cited there for the necessary details for these transformations.

Intermediates of Formula (c) in which Q is Q-4, Q-5 or Q-6 may be prepared by procedures analogous to those outlined above for the imidazole intermediates. A number of references are available which teach chemical transformations and preparation of pyrazole intermediates needed for this invention. For example:

A. N. Kost and I. I. Groundberg, Advan. Heterocyclic Chem 6, 347-429 (1966).

T. L. Jacobs, In "Heterocyclic Compounds" (R. C. Elderfield, ed.), Vol. 5, pp. 45-161, Wiley, N.Y., 1957.

Many of the compounds of Formula (c) in which Q is Q-4 or Q-5, for example 51, can be made by the procedures outlined in Equation 13 and Scheme 5. ##STR35##

The procedure of Equation 13 is suitable for those substituents which can survive the pyrazole metallation; for example R₁₂ is H or CH₃, R₁₀ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl or SO₂ NR₂₀ R₂₁.

Metallation reactions of pyrazoles are discussed in H. W. Gschwend and H. R. Rodriguez, "Organic Reactions", Vol. 26, p. 23, 24, John Wiley and Sons, Inc., New York, 1979.

For the pyrazoles cited above, as well as pyrazoles with groups sensitive to metallation conditions, the procedure of Scheme 5 can be used. For example, compounds in which R₁₀ and R₁₂ are as defined for Formula I and R₁₁ is H, C₁ -C₃ alkyl, F, Cl, Br, OR₁₆, S(O)₂ NR₂₀ R₂₁ may be prepared. Suitable protecting groups include ##STR36## CH₂ OCH₂ CH₂ OCH₃ and t-butyl. See the previously cited reference for details.

Compounds of Formulas 58 and 59 in which R₁₂ is H or CH₃ and R₁₁ is F, Cl, Br, OR₁₆, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ and R₁₀ is as defined for Example I can also be made from intermediates of Formulas 60 and 61 by using the procedures disclosed for the imidazoles in Schemes 1-4. ##STR37##

Compounds of Formula (c) in which Q is Q-6 and R₁₃ and R₁₄ are H, C₁ -C₃ alkyl, OR₁₆, F, Cl, Br, CO₂ R₂₄, S(O)_(m) R₂₅ and SO₂ NR₂₀ R₂₁ and R₁₅ is H or CH₃ are made by metallation at the appropriate pyrazole intermediate 64 as shown in Scheme 6. ##STR38##

The chlorosulfonation of pyrazoles 62 and conversion to sulfonamides 64 in which R₁₃ is H, F, Cl, Br or OR₁₆ where R₁₆ is C₁ -C₃ alkyl is carried out by procedures taught in U.S. Pat. No. 3,665,009.

Protection of the pyrazole ring can be accomplished using the tetrahydropyranyl group ##STR39## (TPE) or --CH₂ OCH₂ CH₂ OCH₃ (MEM). For details of this procedure with (TPE) see H. W. Gschwend and H. R. Rodriguez "Organic Reactions", Vol. 26, p. 24, John Wiley and Sons, Inc., New York, 1979. For details of this procedure with (MEM) see E. J. Corey, J. L. Grus and P. Ulrich, Tet. Let., 809 (1976).

The lithiation of protected pyrazoles and subsequent reactions with electrophiles is taught in H. W. Gschwend and H. R. Rodriguez "Organic Reactions", Vol. 26, p. 24, John Wiley and Sons, Inc., New York, 1979.

Further reaction of 67-71 to produce the appropriate sulfonamide intermediates of this invention is shown in Equations 14-16. ##STR40##

Deprotection of the sulfonamide and pyrazole is accomplished with an acid such as trifluoroacetic acid. Use of HCl in an alcohol R₂₄ OH leads simultaneously to esterification and deprotection to yield sulfonamide 72. Alkylation of 72 with CH₃ I under conditions well known to those skilled in the art leads to additional intermediates 73.

Alkylthio, alkylsulfinyl and alkylsulfonyl analogs are produced from 68 using the procedure of Equations 15 or 15a. Details of this type of transformation can be found in U.S. Ser. No. 345,935, filed Feb. 8, 1982. ##STR41##

The halo derivatives 79 and 80 are obtained from 69 by deprotection as shown in Equation 16. ##STR42## Treatment of heteroaryllithium reagents with halogens is well known in the art. Details are available in H. W. Gschwend and H. R. Rodriguez "Organic Reactions", Vol. 26, John Wiley and Sons, Inc., New York, 1979. Using similar procedures, the analogous compounds in which R₁₄ is C₁ -C₃ alkyl 81 and SO₂ NR₂₀ R₂₁ 82 are produced. ##STR43##

Agriculturally suitable salts of compounds of Formula I are also useful herbicides and can be prepared in a number of ways known to the art. For example, metal salts can be made by treating compounds of Formula I with a solution of alkali or alkaline earth metal salt having a sufficiently basic anion (e.g., hydroxide, alkoxide, carbonate or hydride). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of one cation for another. Cationic exchange can be effected by direct treatment of an aqueous solution of a salt of a compound of Formula I (e.g., alkali metal or quaternary amine salt) with a solution containing the cation to be exchanged. This method is most effective when the desired salt containing the exchanged cation is insoluble in water, e.g., a copper salt, and can be separated by filtration.

Exchange may also be effected by passing an aqueous solution of a salt of a compound of Formula I (e.g., an alkali metal or quaternary amine salt) through a column packed with a cation exchange resin containing the cation to be exchanged. In this method, the cation of the resin is exchanged for that of the original salt and the desired product is eluted from the column. This method is particularly useful when the desired salt is water-soluble, e.g., a potassium, sodium or calcium salt.

Acid addition salts, useful in this invention, can be obtained by reacting a compound of Formula I or II with a suitable acid, e.g., p-toluenesulfonic acid, trichloroacetic acid or the like.

The preparation of the compounds of this invention is further illustrated by the following specific examples. Unless otherwise indicated, temperatures are in degrees centigrade.

EXAMPLE 1 1-Ethyl-1H-imidazole-2-thiol

52.2 g of Ethylisothiocyanate was added dropwise to 79.8 g of aminoacetaldehyde diethyl acetal in 600 ml of ethanol. After the addition was complete, the mixture was heated to reflux for thirty minutes. The ethanol was removed at reduced pressure on a rotary evaporator. One liter of 10% HCl was added, and the mixture was heated to reflux for thirty minutes and then cooled to room temperature. The pH of the solution was then adjusted to 3 with 50% NAOH. The product was extracted with CH₂ Cl₂. The extracts were then dried with MgSO₄, filtered and concentrated on a rotary evaporator. The crude product was chromatographed on silica with 75% ethyl acetate hexane. 18.4 g of the title compound, a solid with m.p. 71°-72°, was obtained.

EXAMPLE 2 1-Ethyl-1H-imidazole-2-sulfonamide

To 17.0 g 1-ethyl-1H-imidazole-2-thiol in 180 ml 2N HCl cooled to 0° to -8° was added dropwise 19.3 ml of Cl₂. The temperature of the reaction was maintained at less than 10° during the addition. The reaction was stirred for about thirty minutes at 0°-10° after the addition was complete. Enough 50% NaOH was added dropwise to the reaction while maintaining the temperature, to raise the pH to 4.0. The white precipitate which formed was filtered and added to a mixture of 100 ml concentrated aqueous ammonia cooled to 0° to 10° C. The mixture was stirred for thirty minutes and then concentrated on a rotary evaporator. The concentrate was boiled three times with CH₃ CN and the insolubles were filtered and discarded. The CH₃ CN extracts were dried over MgSO₄, filtered and concentrated on a rotary evaporator.

11.8 g of the title compound, a white solid with m.p. 123°-125°, was obtained.

EXAMPLE 3 1-Ethyl-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1H-imidazole-2-sulfonamide (I; Q=Q-1, R₁ =C₂ H₅, R₂ =R₃ =H; A=A-1, Z=CH, X=OCH₃, Y=CH₃ ; R=H)

1.75 g of 1-Ethyl-1H-imidazole-2-sulfonamide in 80 ml of dry CH₂ Cl₂ at ambient temperature under N₂ was treated dropwise with 6.0 ml of a 2.0M solution in hexane of (CH₃)₃ Al. The mixture was stirred for a period of fifteen to thirty minutes. 1.97 g of methyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate was then added and the mixture was refluxed for a period of sixteen hours. Enough of a 5% solution of aqueous acetic acid was then added to lower the pH to 3.0. The crude reaction mixture was extracted three times with CH₂ Cl₂. The extracts were dried with MgSO₄, filtered and concentrated on a rotary evaporator. The concentrate was boiled with hot ethyl acetate and the product was filtered to yield 0.8 g of the title compound, a white solid with m.p. 178°-179°(d).

EXAMPLE 4 1-Methylpyrazole-3-sulfonyl chloride

To 120 ml of water and 120 ml of 12N hydrochloric acid was added 45 g of 1-methylpyrazole-3-amine at -10° C. followed by the dropwise addition of 33.9 g sodium nitrite dissolved in 75 ml water. The temperature was maintained at -10° C. and the mixture was stirred for an additional half hour after the additions were completed.

The above solution was then added portionwise with stirring at -10° C. to a mixture containing 348 ml acetic acid, 5.8 g of CuCl and 48 ml (liquified) of sulfur dioxide. After being stirred for one hour at -10° C., the reaction mixture was allowed to warm to 10° C. and was poured into 1500 ml of ice and water. The resultant mixture was extracted three times with 500 ml portions of methylene chloride. The extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to yield a red oil. This material was used for the preparation of 1-methylpyrazole-3-sulfonamide without further purification.

EXAMPLE 5 1-Methylpyrazole-3-sulfonamide

A mixture containing chloroform (100 ml), 13.6 g of 1-methylpyrazole-3-sulfonyl chloride and 13.6 g ammonium carbonate was heated to reflux for six hours, cooled, filtered and the solid was washed with water. The water-insoluble solid which was recrystallized from 50% ethanol-water melted at 149°-151° and showed absorption peaks in the infrared at 3100 and 3200 cm⁻¹, consistent for the NH₂ in the desired product.

Anal. Calc. for C₄ H₇ N₃ O₂ S: C, 29.8; H, 4.38; N, 26.07; S, 19.9. Found: C, 29.3; H, 4.6; N, 25.3; S, 19.2.

EXAMPLE 6 5-Bromo-1-methyl-1H-imidazole-1-sulfonamide

20 ml of chlorosulfonic acid was added dropwise to 6.0 g of 1H-imidazole-5-bromo-1-methyl with stirring at room temperature. The reaction mixture was heated to 100° C. for 16 hours then 140° C. for 4 hours. The reaction mixture was cooled to 0° C. and poured over cracked ice. The resulting tan solid was collected by filtration and dried under vacuum. This crude sulfonyl chloride (m.p. 84°-86° C.) was added to 200 ml of anhydrous ammonia and allowed to sit overnight at ambient temperature. Excess ammonia was removed under a flow of nitrogen and the resulting solid was crystallized from 25 ml of water yielding 3.2 g of the desired sulfonamide melting at 204°-205.5° C.

EXAMPLE 7 1,3-Dimethylpyrazole-4-sulfonamide

59 g (0.615 mmol) of 1,3-dimethylpyrazole is added slowly to 300 g (2.5 mmol) of chlorosulfonic acid at 0° C. The reaction is warmed to 90° C. for 3 hours, cooled and poured onto 500 g of ice. The aqueous solution is extracted with 3×100 ml of ether. The organic extract is dried over anhydrous sodium sulfate and filtered. The ether solution is added dropwise to a solution of 55 grams of anhydrous ammonia (2.5 mmol) in 250 ml of ether. After standing overnight, water is added and the layers separated. The aqueous solution is extracted with ethyl acetate, the organic solutions combined and dried over anhydrous sodium sulfate. After removal of the drying agent, the solvent is removed in vacuo giving 20.5 g of product, m.p.=97°-105° C.

EXAMPLE 8 N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-dimethylpyrazol-4-sulfonamide (I; Q=Q-6, R₁₃ =R₁₅ =CH₃, R₁₄ =H; A=A-1, Z=CH, X=OCH₃, Y=CH₃ ; R=H)

1,3-Dimethylpyrazole-4-sulfonamide (1.75 g, 10 mmol) is placed in 100 ml of 1,2-dichloroethane. Trimethylaluminum in toluene (2M, 10 ml) is added. The reaction is brought to reflux and methyl 4-methoxy-6-methyl-2-aminopyrimidine carbamate (2.0 g, 10 mmols) is added. After refluxing overnight, the reaction is cooled, poured into ice water and treated with 60 ml of 10% HCl. The layers are separated, the organic phase extracted with methylene chloride, and the organic solutions combined. The organic solution is dried with anhydrous sodium sulfate and decolorized with charcoal. The solvent is removed in vacuo. The solid is triturated with ether and collected giving 1.5 g, m.p.=207°-210° C.

By using the procedures of Examples 1-8 and the general procedures taught in Equations 1-16 and Schemes 1-6, the following compounds can be prepared.

                                      TABLE Ia                                     __________________________________________________________________________      ##STR44##                                                                     R.sub.1           R.sub.2                                                                           R.sub.3                                                                           R  Z  X    Y       m.p. (°C.)                   __________________________________________________________________________     H                 H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3          H  H  H  CH CH.sub.3                                                                            CH.sub.3                                                                               174-178°                     CH.sub.3          H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                                                              182-183°                     CH.sub.3          H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                                                              158-165°                     CH.sub.3          H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                                                              170-172°                     CH.sub.3 CH.sub.2 H  H  H  CH CH.sub.3                                                                            CH.sub.3                                                                               196-197°(d)                  CH.sub.3 CH.sub.2 H  H  H  CH CH.sub.3                                                                            OCH.sub. 3                                                                             178-179°(d)                  CH.sub.3 CH.sub.2 H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                                                              186-187°                     CH.sub.3 CH.sub.2 H  H  H  N  CH.sub.3                                                                            CH.sub.3                                                                               141-143°(d)                  CH.sub.3 CH.sub.2 H  H  H  N  CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 CH.sub.2 H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                                                              160-161°                     CH.sub.3 CH.sub.2 H  H  H  CH Cl   OCH.sub.3                                   CH.sub.3 CH.sub.2 CH.sub.2                                                                       H  H  H  CH CH.sub.3                                                                            CH.sub.3                                                                               178-180°                     CH.sub.3 CH.sub.2 CH.sub.2                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                                                              156-159.5°                   CH.sub.3 CH.sub.2 CH.sub.2                                                                       H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.3 CH.sub.2 CH.sub.2                                                                       H  H  H  CH Cl   OCH.sub.3                                   CH.sub.3 CH.sub.2 CH.sub.2                                                                       H  H  H  N  CH.sub.3                                                                            CH.sub.3                                                                               122-124°                     CH.sub.3 CH.sub.2 CH.sub.2                                                                       H  H  H  N  CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 CH.sub.2 CH.sub.2                                                                       H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                                                              172-174°                     (CH.sub.3).sub.2 CH                                                                              H  H  H  N  CH.sub.3                                                                            CH.sub.3                                    (CH.sub.3).sub.2 CH                                                                              H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                                                              170-172°                     (CH.sub.3).sub.2 CH                                                                              H  H  H  N  OCH.sub.3                                                                           CH.sub.3                                    (CH.sub.3).sub.2 CH                                                                              H  H  H  CH CH.sub.3                                                                            CH.sub.3                                                                               185-186°(d)                  (CH.sub.3).sub.2 CH                                                                              H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                                                              166-167°                     (CH.sub.3).sub.2 CH                                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                                                              157-158°(d)                  (CH.sub.3).sub.2 CH                                                                              H  H  H  CH Cl   OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.3                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.3                                                                        H  H  H  CH CH.sub.3                                                                            CH.sub.3                                    CH.sub.3 (CH.sub.2).sub.3                                                                        H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.3                                                                        H  H  H  CH Cl   OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.3                                                                        H  H  H  N  CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.3                                                                        H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                    ##STR45##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   (CH.sub.3).sub.3 C                                                                               H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR46##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.4                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR47##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   (CH.sub.3).sub.3 CCH.sub.2                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR48##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR49##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.5                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR50##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR51##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 CHCHCH.sub.2                                                                            H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR52##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 CHCHCH.sub.2CH.sub.2                                                                    H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR53##        H  H  H  CH CH   OCH                                         CHCCH.sub.2CH.sub.2                                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR54##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR55##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR56##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.7                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 (CH.sub.2).sub.6                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR57##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR58##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR59##        H  H  H  CH CH.sub.3                                                                            CH.sub.3                                                                               182-184°(d)                   ##STR60##        H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                                                              131-134°(d)                   ##STR61##        H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                                                              172-174°(d)                   ##STR62##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR63##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR64##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR65##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR66##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub. 2CHCH.sub.2                                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2CHCH.sub.2                                                                               H  H  H  CH CH.sub.3                                                                            CH.sub.3                                    CH.sub.2CHCH.sub.2                                                                               H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.2CHCH.sub.2                                                                               H  H  H  CH Cl   OCH.sub.3                                   CH.sub.2CHCH.sub.2                                                                               H  H  H  N  CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2CHCH.sub.2                                                                               H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.2CHCH.sub.2                                                                               H  H  H  N  CH.sub.3                                                                            CH.sub.3                                    CH.sub.2CCH       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2CCH       H  H  H  CH CH.sub.3                                                                            CH.sub.3                                    CH.sub.2CCH       H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.2CCH       H  H  H  CH Cl   OCH.sub.3                                   CH.sub.2CCH       H  H  H  N  CH.sub.3                                                                            CH.sub.3                                    CH.sub.2CCH       H  H  H  N  OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.2CCH       H  H  H  N  CH.sub.3                                                                            OCH.sub.3                                   CF.sub.3          H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 CF.sub.3 H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CF.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR67##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR68##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CF.sub.2 HCH.sub.2CH.sub.2                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR69##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR70##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CCl.sub.3CH.sub.2CH.sub.2                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 BrCH.sub.2CH.sub.2                                                                      H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CF.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   H.sub.2 CF(CH.sub.2).sub.4                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   H.sub.2 CF(CH.sub.2).sub.5                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 OCH.sub.2 CH.sub.2                                                                      H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 CH.sub.2 OCH.sub.2                                                                      H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 OCH.sub.2                                                                               H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   (CH.sub.3).sub.2 CHOCH.sub.2 CH.sub.2                                                            H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2                                                             H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 COCH.sub.3                                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 COCH.sub.2 CH.sub.3                                                                     H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 COCH(CH.sub.3).sub.2                                                                    H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR71##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR72##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR73##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR74##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR75##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR76##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR77##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR78##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR79##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR80##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR81##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR82##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR83##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR84##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR85##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR86##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR87##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR88##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR89##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR90##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR91##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR92##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR93##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR94##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR95##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR96##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR97##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR98##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR99##        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR100##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR101##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR102##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR103##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR104##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR105##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR106##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR107##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2SO.sub.2N(CH.sub.3).sub.2                                                                H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR108##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2SO.sub.2N(CH.sub.3)CH.sub.2 CH.sub.3                                                     H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2N(CH.sub.3).sub.2                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                          H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2SO.sub.2 CH.sub.3                                                                        H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 SO.sub.2 CF.sub.3                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.3                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 CF.sub.3 H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 CH.sub.2 CH.sub.3                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2CH(CH.sub.3).sub.2                                                                       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR109##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2SO.sub.2 CH(CH.sub.3).sub.2                                                              H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   SO.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            CH.sub.3                                    SO.sub.2 CH.sub.3 H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                   SO.sub.2 CH.sub.3 H  H  H  CH Cl   OCH.sub.3                                   SO.sub.2 CF.sub.3 H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                   SO.sub.2 CF.sub.3 H  H  H  CH Cl   OCH.sub.3                                   CH.sub.2 SO.sub.2 CH.sub.3                                                                       H  H  H  CH OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.2 SO.sub.2 CH.sub.3                                                                       H  H  H  CH Cl   OCH.sub.3                                    ##STR110##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR111##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR112##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR113##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR114##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR115##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                    ##STR116##       H  H  H  CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 CH.sub.3 H  H  CH.sub.3                                                                          CH CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 CH.sub.3 H  H  CH.sub.3                                                                          CH OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.2 CH.sub.3 H  H  CH.sub.3                                                                          CH CH.sub.3                                                                            CH.sub.3                                    CH.sub.2 CH.sub.3 H  H  CH.sub.3                                                                          N  OCH.sub.3                                                                           OCH.sub.3                                   CH.sub.2 CH.sub.3 H  H  CH.sub. 3                                                                         N  CH.sub.3                                                                            OCH.sub.3                                   CH.sub.2 CH.sub.3 CH.sub.3                                                                          H  H  CH CH.sub.3                                                                            CH.sub.3                                    CH.sub.2 CH.sub.3 H  CH.sub.3                                                                          H  CH CH.sub.3                                                                            CH.sub.3                                    CH.sub.2 CH.sub.3 CH.sub.3                                                                          CH.sub.3                                                                          H  CH CH.sub.3                                                                            CH.sub.3                                    CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            CH.sub.2 CH.sub.3                           CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCH.sub.2 CH.sub.3                          CH.sub.2 CH.sub.3 H  H  H  N  CH.sub.3                                                                            CH.sub.2 OCH.sub.3                          CH.sub.2 CH.sub.3 H  H  H  N  CH.sub.3                                                                            CH(OCH.sub.3).sub.2                         CH.sub.2 CH.sub.3 H  H  H  CH OCH.sub.3                                                                           NH.sub.2                                    CH.sub.2 CH.sub.3 H  H  H  N  OCH.sub.3                                                                           CH.sub.3 NH                                 CH.sub.2 CH.sub.3 H  H  H  N  OCH.sub.3                                                                           (CH.sub.3).sub.2 N                          CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         CH.sub.3                                    CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCH.sub.3                                   CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         CH.sub.3                                    CH.sub.2 CH.sub.3 H  H  H  CH SCF.sub.2 H                                                                         CH.sub.3                                    CH.sub.2 CH.sub.3 H  H  H  CH SCF.sub.2 H                                                                         OCH.sub.3                                   CH.sub.2 CH.sub.3 H  H  H  CH SCF.sub.2 H                                                                         OCF.sub.3                                   CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCH.sub.2 CF.sub.3                          CH.sub.2 CH.sub.3 H  H  H  CH OCH.sub.3                                                                           OCH.sub.2 CF.sub.3                          CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCF.sub.3                                   CH.sub.2 CH.sub.3 H  H  H  CH OCH.sub.3                                                                           OCF.sub.3                                   CH.sub.2 CH.sub.3 H  H  H  N  CH.sub.3                                                                            OCF.sub.3                                   CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCF.sub.2 CHClF                             CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                        CH.sub.2 CH.sub.3 H  H  H  CH OCH.sub.3                                                                           OCF.sub.2 CF.sub.2 H                        CH.sub.2 CH.sub.3 H  H  H  N  CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                        CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCF.sub.2 CHFCF.sub.3                       CH.sub.2 CH.sub.3 H  H  H  CH OCH.sub.3                                                                           OCF.sub.2 CHFCF.sub.3                       CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                           CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CH.sub.3                          CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                          CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         CH(OCH.sub.3).sub.2                         CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                          CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCF.sub.3                                   CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         NH.sub.2                                    CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         NHCH.sub.3                                  CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                           CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 H                                 CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHClF                             CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                             CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CF.sub.2 H                        CH.sub.2 CH.sub.3 H  H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                       CH.sub.2 CH.sub.3 H  H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                        CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                           CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                          CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                          CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         NH.sub.2                                    CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                           CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                             CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                       CH.sub.2 CH.sub.3 H  H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 H                                 CH.sub.2 CH.sub.3 H  H  H  N  CH.sub.3                                                                            OCF.sub.2 H                                 __________________________________________________________________________

                  TABLE Ib                                                         ______________________________________                                          ##STR117##                                                                    R.sub.1   R.sub.2                                                                              R.sub.3 R   A      Y.sup.1                                                                               m.p.(°                        ______________________________________                                                                                   C.)                                  CH.sub.2 CH.sub.3                                                                        H     H       H   A-2    H                                           CH.sub.2 CH.sub.3                                                                        H     H       H   A-2    CH.sub.3                                    CH.sub.2 CH.sub.3                                                                        H     H       H   A-2    Cl                                          CH.sub.2 CH.sub.3                                                                        H     H       H   A-2    OCH.sub.3                                   CH.sub.2 CH.sub.3                                                                        H     H       H   A-2    OCF.sub.2 H                                 CH.sub.2 CH.sub.3                                                                        H     H       H   A-3    Cl                                          CH.sub.2 CH.sub.3                                                                        H     H       H   A-3    CH.sub.3                                    CH.sub.2 CH.sub.3                                                                        H     H       H   A-3    OCH.sub.3                                   CH.sub.2 CH.sub.3                                                                        H     H       H   A-3    OCF.sub.2 H                                 CH.sub.2 CH.sub.3                                                                        H     H       H   A-4    H                                           CH.sub.2 CH.sub.3                                                                        H     H       H   A-4    Cl                                          CH.sub.2 CH.sub.3                                                                        H     H       H   A-4    CH.sub.3                                    CH.sub.2 CH.sub.3                                                                        H     H       H   A-4    OCH.sub.3                                   CH.sub.2 CH.sub.3                                                                        H     H       H   A-4    OCF.sub.2 H                                 ______________________________________                                    

                  TABLE Ic                                                         ______________________________________                                          ##STR118##                                                                                                                m.p.                               R.sub.1 R.sub.2                                                                              R.sub.3                                                                              R   A    X.sup.2 Y.sup.2                                                                               X.sup.3 (°C.)               ______________________________________                                         CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  OCH.sub.3                                                                              CH.sub.3                                                                              --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  CH.sub.3                                                                               CH.sub.2 CH.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  CH.sub.3                                                                               CH.sub.2 CF.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  OCH.sub.3                                                                              CH.sub.3                                                                              --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  OCH.sub.3                                                                              CH.sub.2 CH.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  OCH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  CH.sub.2 CH.sub.3                                                                      CH.sub. 3                                                                             --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  CH.sub.2 CH.sub.3                                                                      CH.sub.2 CH.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  CH.sub.2 CH.sub.3                                                                      CH.sub.2 CF.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  OCH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                              --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  OCH.sub.2 CH.sub.3                                                                     CH.sub.2 CH.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  OCH.sub.2 CH.sub.3                                                                     CH.sub.2 CF.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  SCH.sub.3                                                                              CH.sub.3                                                                              --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  SCH.sub.3                                                                              CH.sub.2 CH.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  SCH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  SCH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                              --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  SCH.sub.2 CH.sub.3                                                                     CH.sub.2 CH.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-5  SCH.sub.2 CH.sub.3                                                                     CH.sub.2 CF.sub.3                                                                     --                                 CH.sub.2 CH.sub.3                                                                      H     H     H   A-6  --      --     OCH.sub.3                          CH.sub.2 CH.sub.3                                                                      H     H     H   A-6  --      --     CH.sub.3                           ______________________________________                                    

                                      TABLE IIa                                    __________________________________________________________________________      ##STR119##                                                                    __________________________________________________________________________     R.sub.6       R.sub.5    R.sub.4                                                                           R  Z  X    Y       m.p.(°                   __________________________________________________________________________                                                    C.)                             CH.sub.3      H          CH.sub.3                                                                          H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      H          H  H  CH CH.sub.3                                                                            OCH.sub.3                                                                              158-163°                 CH.sub.3      H          H  H  CH CH.sub.3                                                                            CH.sub.3                                                                               171-179° 183                                                            -CH.sub.3 CH.sub.2 H H H CH                                                    1CH.sub.3 OCH.sub.3             CH.sub.3 CH.sub.2 CH.sub.2                                                                   H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               (CH.sub.3).sub.2 CH                                                                          H          H  H  CH CH.sub.3                                                                            OCH.sub.3                                ##STR120##   H          H  H  CH CH.sub.3                                                                            OCH.sub.3                                ##STR121##   H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               (CH.sub.3).sub.3 C                                                                           H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 CHCH H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.2 CHCH.sub.2                                                                          H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3CHCHCH.sub.2                                                                         H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               HCCCH.sub.2   H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3CCCH.sub.2                                                                           H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CF.sub.3      H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CF.sub.3 CH.sub.2                                                                            H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               H.sub.2 CFCH.sub.2 CH.sub.2                                                                  H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               ClCH.sub.2 CH.sub.2 CH.sub.2                                                                 H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               HCFClCH.sub.2 CH.sub.2 CH.sub.2                                                              H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               Br(CH.sub.2).sub.4                                                                           H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 OCH.sub.2                                                                           H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 OCH.sub.2 CH.sub.2                                                                  H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.3                                                                            H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.3                                                                   H          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH(CH.sub.3).sub.2                                                                  H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CHCH.sub.2                                                                 H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2CCH                                                                         H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CHCHCH.sub.3                                                               H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2CCCH.sub.3                                                                  H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                         H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub. 2 CH.sub.2 Cl                                                               H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.3).sub.2                                                                   H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                      H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                          H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH.sub.3                                                                            H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CF.sub.3                                                                            H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH.sub.2 CH.sub.3                                                                   H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                          H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH(CH.sub.3).sub.2                                                                  H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 CH.sub.2                                                                            H          H  H  CH CH.sub.3                                                                            CH.sub.3                                CH.sub.3 CH.sub.2                                                                            H          H  H  CH Cl   OCH.sub.3                               CH.sub.3 CH.sub.2                                                                            H          H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                            H          H  H  N  OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                            H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CH.sub. 3 CH.sub.2                                                                           H          H  H  N  CH.sub.3                                                                            CH.sub.3                                CH.sub.3 CH.sub.2                                                                            H          H  CH.sub.3                                                                          CH OCH.sub.3                                                                           CH.sub.3                                CH.sub.3 CH.sub.2                                                                            H          H  CH.sub.3                                                                          CH CH.sub.3                                                                            CH.sub.3                                CH.sub.3 CH.sub.2                                                                            H          H  CH.sub.3                                                                          CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                            H          H  CH.sub.3                                                                          N  OCH.sub.3                                                                           OCH.sub.3                               OCH.sub.3     H          H  CH.sub.3                                                                          N  OCH.sub.3                                                                           CH.sub.3                                CH.sub.3      CH.sub.3   H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      Cl         H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CO.sub.2 CH.sub.3                                                                         H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      NO.sub.2   H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      SO.sub.2 N(CH.sub.3).sub.2                                                                H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.3                                                                            CH.sub.3   H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.3).sub.2                                                                   CH.sub.3   H  H  CH CH.sub.3                                                                            OCH.sub.3                               H             F          H  H  CH CH.sub.3                                                                            OCH.sub.3                               H             Br         H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CH.sub.3 CH.sub.2                                                                         H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CH.sub.3 CH.sub.2 CH.sub.2                                                                H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CH.sub.3 (CH.sub.2).sub.3                                                                 H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      (CH.sub.3).sub.2 CHCH.sub.2                                                               H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3                                                                                      ##STR122##                                                                               H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CO.sub.2 CH.sub.3                                                                         H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CO.sub.2 CH.sub.2 CH.sub.3                                                                H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      CO.sub.2 CH(CH.sub.3).sub.2                                                               H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3      SO.sub.2 N(CH.sub.3).sub.2                                                                H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                   H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SO.sub.2 N(CH.sub.2 CH.sub.3)                                                             H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SCH.sub.3  H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SOCH.sub.3 H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SO.sub.2 CH.sub.2 CH.sub.3                                                                H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                       H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SCH.sub.2 CH.sub.3                                                                        H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SCH.sub.2 CH.sub.2 CH.sub.3                                                               H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3      SO.sub.2 CH(CH.sub.3).sub.2                                                               H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                            H          H  H  CH CH.sub.3                                                                            CH.sub.3 CH.sub.2                       H             H          H  H  CH CH.sub.3                                                                            CH.sub.3                                                                               240-242                         H             H          H  H  CH CH.sub.3                                                                            OCH.sub.3                                                                              207-208.5                       H             H          H  H  CH OCH.sub.3                                                                           OCH.sub.3                                                                              211-216                         H             H          H  H  N  CH.sub.3                                                                            CH.sub.3                                                                               188-193                         H             H          H  H  N  CH.sub.3                                                                            OCH.sub.3                               H             H          H  H  N  OCH.sub.3                                                                           OCH.sub.3                                                                              150-158                         CH.sub.3 CH.sub.2                                                                            H          H  H  CH CH.sub.3                                                                            OCH.sub.2 CH.sub.3                      CH.sub.3 CH.sub.2                                                                            H          H  H  CH CH.sub.3                                                                            CH.sub.2 OCH.sub.3                      CH.sub.3 CH.sub.2                                                                            H          H  H  CH CH.sub.3                                                                            CH.sub.2 (OCH.sub.3).sub.2              CH.sub.3 CH.sub.2                                                                            H          H  H  CH OCH.sub.3                                                                           NH.sub.2                                CH.sub.3 CH.sub.2                                                                            H          H  H  N  OCH.sub.3                                                                           NHCH.sub.3                              CH.sub.3 CH.sub.2                                                                            H          H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                       CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         CH.sub.3                                CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCH.sub.3                               CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         CH.sub.3                                CH.sub.2 CH.sub.3                                                                            H          H  H  CH SCF.sub.2 H                                                                         CH.sub.3                                CH.sub.2 CH.sub.3                                                                            H          H  H  CH SCF.sub.2 H                                                                         OCH.sub.3                               CH.sub.2 CH.sub.3                                                                            H          H  H  CH SCF.sub.2 H                                                                         OCF.sub.3                               CH.sub.2 CH.sub.3                                                                            H          H  H  CH CH.sub.3                                                                            OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCH.sub.3                                                                           OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                            H          H  H  CH CH.sub.3                                                                            OCF.sub.3                               CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCH.sub.3                                                                           OCF.sub.3                               CH.sub.2 CH.sub.3                                                                            H          H  H  N  CH.sub.3                                                                            OCF.sub. 3                              CH.sub.2 CH.sub.3                                                                            H          H  H  CH CH.sub.3                                                                            OCF.sub.2 CHClF                         CH.sub.2 CH.sub.3                                                                            H          H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCH.sub.3                                                                           OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                            H          H  H  N  CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                            H          H  H  CH CH.sub.3                                                                            OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCH.sub.3                                                                           OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                       CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CH.sub.3                      CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                      CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         CH(OCH.sub.3).sub.2                     CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCF.sub.3                               CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         NH.sub. 2                               CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         NHCH.sub.3                              __________________________________________________________________________     R.sub.1       R.sub.2    R.sub.3                                                                           R  Z  X    Y       m.p.(°C.)                __________________________________________________________________________     CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                       CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 H                             CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHClF                         CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                         CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                            H          H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub.3                                                                            H          H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                       CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                      CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         NH.sub. 2                               CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                       CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                         CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub.3                                                                            H          H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 H                             CH.sub.2 CH.sub.3                                                                            H          H  H  N  CH.sub.3                                                                            OCF.sub.2 H                             __________________________________________________________________________

                  TABLE IIb                                                        ______________________________________                                          ##STR123##                                                                    R.sub.6 R.sub.5    R.sub.4                                                                               R   A    Y.sup.1                                                                               m.p.(°C.)                     ______________________________________                                         CH.sub.3 CH.sub.2                                                                      H          H      H   A-2  H                                           CH.sub.3 CH.sub.2                                                                      H          H      H   A-2  Cl                                          CH.sub.3 CH.sub.2                                                                      H          H      H   A-2  CH.sub.3                                    CH.sub.3 CH.sub.2                                                                      H          H      H   A-2  OCH.sub.3                                   CH.sub.3 CH.sub.2                                                                      H          H      H   A-2  OCF.sub.2 H                                 H       CO.sub.2 CH.sub.3                                                                         H      H   A-3  H                                           H       CO.sub.2 CH.sub.3                                                                         H      H   A-3  Cl                                          H       CO.sub.2 CH.sub.3                                                                         H      H   A-3  CH.sub.3                                    H       CO.sub.2 CH.sub.3                                                                         H      H   A-3  OCH.sub.3                                   CH.sub.3 CH.sub.2                                                                      H          H      H   A-2  OCF.sub.2 H                                 H       SO.sub.2 N(CH.sub.3).sub.2                                                                H      H   A-4  H                                           H       SO.sub.2 N(CH.sub.3).sub.2                                                                H      H   A-4  Cl                                          H       SO.sub. 2 N(CH.sub.3).sub.2                                                               H      H   A-4  CH.sub.3                                    H       SO.sub.2 N(CH.sub.3).sub.2                                                                H      H   A-4  OCH.sub.3                                   CH.sub.3 CH.sub.2                                                                      H          H      H   A-4  OCF.sub.2 H                                 ______________________________________                                    

                                      TABLE IIc                                    __________________________________________________________________________      ##STR124##                                                                    R.sub.6                                                                          R.sub.5                                                                              R.sub.4                                                                          R A  X.sup.2                                                                               Y.sup.2                                                                              X.sup.3                                                                            m.p. (°C.)                              __________________________________________________________________________     H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               OCH.sub.3                                                                             CH.sub.3                                                                             --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               OCH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               OCH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               CH.sub.3                                                                              CH.sub.3                                                                             --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               CH.sub.3                                                                              CH.sub.2 CH.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               CH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               CH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                             --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               CH.sub.2 CH.sub.3                                                                     CH.sub.2 CH.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               CH.sub.2 CH.sub.3                                                                     CH.sub.2 CF.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                             --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CF.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               SCH.sub.3                                                                             CH.sub.3                                                                             --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               SCH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               SCH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               SCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                             --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               SCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-5                                                                               SCH.sub.2 CH.sub.3                                                                    CH.sub.2 CF.sub.3                                                                    --                                                 H SO.sub.2 CH.sub.3                                                                    H H A-6                                                                               --     --    OCH.sub.3                                          H SO.sub.2 CH.sub.3                                                                    H H A-6                                                                               --     --    CH.sub.3                                           __________________________________________________________________________

                                      TABLE IIIa                                   __________________________________________________________________________      ##STR125##                                                                    R.sub.8     R.sub.9                                                                               R.sub.7                                                                          R Z  X    Y        m.p. (°C.)                      __________________________________________________________________________     H           CH.sub.3                                                                              CH.sub.3                                                                         H CH CH.sub.3                                                                            OCH.sub.3                                       H           CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CH.sub.3    CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CH.sub.3 CH.sub.2                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CH.sub.3 CH.sub.2 CH.sub.2                                                                 CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CH.sub.3 (CH.sub.2).sub.3                                                                  CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       (CH.sub.3).sub.2 CHCH.sub.2                                                                CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       (CH.sub.3).sub.3 C                                                                         CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                        ##STR126## CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CH.sub.2CHCH.sub.2                                                                         CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CH.sub.3 CHCHCH.sub.2                                                                      CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       HCCCH.sub.2 CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CH.sub.3 CCCH.sub.2                                                                        CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       OCH.sub.3   CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       OCH.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       OCH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       OCH.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       NO.sub.2    CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       F           CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       Cl          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CO.sub.2 CH.sub.2 CHCH.sub.2                                                               CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SCH.sub.3   CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SOCH.sub.3  CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SCH.sub.2 CH.sub.3                                                                         CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SCH.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SCH(CH.sub.3).sub.2                                                                        CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SO.sub.2 CH(CH.sub.3).sub.2                                                                CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                    CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                     H H CH CH.sub.3                                                                            OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            CH.sub.3                                        CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCH.sub.3                                                                           OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH Cl   OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3                                                                            CH.sub.3                                        CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3 O                                                                          CH.sub.3                                        CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3 O                                                                          CH.sub.3 O                                      CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3 O                                                                          NH.sub.2                                        CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3 O                                                                          NHCH.sub.3                                      CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3 O                                                                          N(CH.sub.3).sub.2                               CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3                                                                            OCH.sub.2 CH.sub.3                              CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3                                                                            CH.sub.2 OCH.sub.3                              CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3                                                                            CH(OCH.sub.3).sub.2                             H           CH.sub.3 CH.sub.2                                                                     H H CH CH.sub.3                                                                            OCH.sub.3                                                                               215-216                                H           SO.sub.2 N(CH.sub.3).sub.2                                                            H H CH CH.sub.3                                                                            OCH.sub.3                                                                               185-188                                H           SO.sub.2 N(CH.sub.3).sub.2                                                            H H N  CH.sub.3                                                                            OCH.sub.3                                                                               118-125                                H           SO.sub.2 N(CH.sub.3).sub.2                                                            H H CH CH.sub.3                                                                            CH.sub.3 195-202                                H           CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                                                               222-224.5                              H           CH.sub.3                                                                              H H N  CH.sub. 3                                                                           CH.sub.3 188-193                                Br          CH.sub.3                                                                              H H CH CH.sub.3                                                                            CH.sub.3 241-243                                Br          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                                                               208-210.5                              Br          CH.sub.3                                                                              H H CH OCH.sub.3                                                                           OCH.sub.3                                                                               205-206                                Br          CH.sub.3                                                                              H H N  CH.sub.3                                                                            CH.sub.3 202.5-204                              Br          CH.sub.3                                                                              H H N  CH.sub.3                                                                            OCH.sub.3                                                                               192-194                                Br          CH.sub.3                                                                              H H N  OCH.sub.3                                                                           OCH.sub.3                                       Br          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCF.sub.2 H                                     Cl          CH.sub.3                                                                              H H CH CH.sub.3                                                                            CH.sub.3 233-235                                Cl          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.3                                                                               204-207                                Cl          CH.sub.3                                                                              H H CH OCH.sub.3                                                                           OCH.sub.3                                                                               170-178                                Cl          CH.sub.3                                                                              H H N  CH.sub.3                                                                            CH.sub.3 200-203                                Cl          CH.sub.3                                                                              H H N  CH.sub.3                                                                            OCH.sub.3                                                                               191-193                                Cl          CH.sub.3                                                                              H H N  OCH.sub.3                                                                           OCH.sub.3                                                                               194-200                                Cl          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCF.sub.2 H                                     Br          H      H H CH CH.sub.3                                                                            CH.sub.3 234.5-237                              Br          H      H H CH CH.sub.3                                                                            OCH.sub.3                                       Br          H      H H CH OCH.sub.3                                                                           OCH.sub.3                                                                               208-215                                Br          H      H H N  CH.sub.3                                                                            CH.sub.3                                        Br          H      H H N  CH.sub.3                                                                            OCH.sub.3                                       Br          H      H H N  OCH.sub.3                                                                           OCH.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         CH.sub.3                                        CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCH.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         CH.sub.3                                        CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH SCF.sub.2 H                                                                         CH.sub.3                                        CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH SCF.sub.2 H                                                                         OCH.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH SCF.sub.2 H                                                                         OCF.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCH.sub.2 CF.sub.3                              CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCH.sub.3                                                                           OCH.sub.2 CF.sub.3                              CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCF.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCH.sub.3                                                                           OCF.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3                                                                            OCF.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCF.sub.2 CHClF                                 CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                            CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCH.sub.3                                                                           OCF.sub.2 CF.sub.2 H                            CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                            CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCF.sub.2 CHFCF.sub.3                           CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCH.sub.3                                                                           OCF.sub.2 CHFCF.sub.3                           CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                               CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCH.sub.2 CH.sub.3                              CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                              CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         CH(OCH.sub.3).sub.2                             CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                              CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCF.sub.3                                       CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub. 2 H                                                                        NH.sub.2                                        CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         NHCH.sub.3                                      CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                               CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCF.sub.2 H                                     CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCF.sub.2 CHClF                                 CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                                 CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCF.sub.2 CF.sub.2 H                            CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                           CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                            CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                               CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                              CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                              CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         NH.sub.2                                        CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                               CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                                 CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                           CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  OCF.sub.2 H                                                                         OCF.sub.2 H                                     CH.sub.2 CH.sub.3                                                                          CH.sub.3                                                                              H H N  CH.sub.3                                                                            OCF.sub.2 H                                     __________________________________________________________________________

                  TABLE IIIb                                                       ______________________________________                                          ##STR127##                                                                    R.sub.8   R.sub.9                                                                               R.sub.7                                                                               R    A    Y.sup.1                                                                               m.p. (°C.)                     ______________________________________                                         SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-2  H                                            SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-2  Cl                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-2  CH.sub.3                                     SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-2  OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-2  OCF.sub.2 H                                  SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-3  H                                            SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-3  Cl                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-3  CH.sub.3                                     SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-3  OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-3  OCF.sub.2 H                                  SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-4  H                                            SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-4  CH.sub.3                                     SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-4  Cl                                           SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-4  OCH.sub.3                                    SO.sub.2 N(CH.sub.3).sub.2                                                               CH.sub.3                                                                              H      H    A-4  OCF.sub.2 H                                  ______________________________________                                    

                                      TABLE IIIc                                   __________________________________________________________________________      ##STR128##                                                                    R.sub.8                                                                              R.sub.9                                                                           R.sub.7                                                                           R  A  X.sup.2                                                                              Y.sup.2                                                                             X.sup.3                                                                            m.p. (°C.)                             __________________________________________________________________________     SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.3                                                                            --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.2 CF.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.3                                                                            --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.2 CF.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                            --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.2 CH.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.2 CF.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.3                                                                            --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.2 CF.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                            --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.2 CH.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.2 CF.sub.3                                                                   --                                                Br    CH.sub.3                                                                          H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.3                                                                            --                                                Br    CH.sub.3                                                                          H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                   --                                                Br    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                   --                                                Br    CH.sub.3                                                                          H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.2 CF.sub.3                                                                   --                                                SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-6                                                                               --    --   OCH.sub.3                                         SO.sub.2 CH.sub.3                                                                    CH.sub.3                                                                          H  H  A-6                                                                               --    --   CH.sub.3                                          Br    CH.sub.3                                                                          H  H  A-6                                                                               --    --   OCH.sub.3                                         Br    CH.sub.3                                                                          H  H  A-6                                                                               --    --   CH.sub.3                                          __________________________________________________________________________

                                      TABLE IVa                                    __________________________________________________________________________      ##STR129##                                                                    R.sub.10     R.sub.11    R.sub.12                                                                          R  Z  X    Y       m.p. (°C.)               __________________________________________________________________________     H            H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 CH.sub.2 CH.sub.2                                                                  H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               (CH.sub.3).sub.2 CH                                                                         H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 (CH.sub.2).sub.3                                                                   H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               (CH.sub.3).sub.2 CHCH.sub.2                                                                 H           H  H  CH CH.sub.3                                                                            OCH.sub.3                                ##STR130##  H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               (CH.sub.3).sub.3 C                                                                          H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.2CHCH.sub.2                                                                          H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 CHCHCH.sub.2                                                                       H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.2CCH  H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3CCCH.sub.2                                                                          H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.3                                                                  H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH(CH.sub.3).sub.2                                                                 H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.2 CHCH.sub.2                                                                H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                     H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.3 CH.sub.3).sub.2                                                         H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CF.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH.sub.2 CH.sub.3                                                                  H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 CH(CH.sub.3).sub.2                                                                 H           H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            CH.sub.3                                CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  CH Cl   OCH.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            CH.sub.3                                CH.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            OCH.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCH.sub.3                                                                           OCH.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3 O                                                                          NHCH.sub.3                              CH.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3 O                                                                          N(CH.sub.3).sub.2                       CO.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            CH.sub.3                                CO.sub.2 CH.sub.3                                                                           H           H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CO.sub.2 CH.sub.3                                                                           H           H  H  CH Cl   OCH.sub.3                               CO.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            CH.sub.3                                CO.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            OCH.sub.3                               CO.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            OCH.sub.2 CH.sub.3                      CO.sub.2 CH.sub.3                                                                           H           H  H  N  OCH.sub.3                                                                           OCH.sub.3                               CO.sub.2 CH.sub.3                                                                           H           H  H  CH Cl   NH.sub.2                                SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  CH CH.sub.3                                                                            CH.sub.3                                SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  CH OCH.sub.3                                                                           OCH.sub.3                               SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  CH Cl   OCH.sub.3                               SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  N  CH.sub.3                                                                            CH.sub.3                                SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  N  CH.sub.3                                                                            OCH.sub.3                               SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  N  CH.sub. 3                                                                           OCH.sub.2 CH.sub.3                      SO.sub.2 N(CH.sub.3).sub.2                                                                  H           H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                       CH.sub.3     CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     CO.sub.2 CH.sub.2 CHCH.sub.2                                                               H  H  CH CH.sub.3                                                                            CH.sub.3                                CH.sub.3     SCH.sub.3   H  H  CH Cl   OCH.sub.3                               CH.sub.3     SCH.sub.2 CH.sub.2 CH.sub.3                                                                H  H  N  OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     SCH.sub.2 CH(CH.sub.3).sub.2                                                               H  H  N  CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SOCH.sub.3  H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                       CH.sub.3     SOCH.sub.2 CH.sub.3                                                                        H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SOCH.sub.2 CH.sub.2 CH.sub.3                                                               H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SO.sub.2 CH.sub.3                                                                          H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SO.sub.2 CH.sub.2 CH.sub.3                                                                 H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SO.sub.2 N(CH.sub.3).sub. 2                                                                H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                    H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                        H  H  CH CH.sub.3                                                                            OCH.sub.3                               H            CH.sub.2 CH.sub.3                                                                          H  H  CH OCH.sub.3                                                                           OCH.sub.3                               H            CH(CH.sub.3).sub.2                                                                         H  H  CH CH.sub.3                                                                            CH.sub.3                                CH.sub.3     F           H  H  CH CH.sub.3                                                                            OCH.sub.3                               H            Cl          H  H  CH Cl   OCH.sub.3                               CH.sub.3     Br          H  H  N  CH.sub.3                                                                            OCH.sub.3                               H            NO.sub.2    H  H  N  OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     OCH.sub.3   H  H  N  CH.sub.3 O                                                                          N(CH.sub.3).sub.2                       CH.sub.3     OCH.sub.2 CH.sub.3                                                                         H  H  CH CH.sub.3 O                                                                          NHCH.sub.3                              CH.sub.3     OCH.sub.2 CH.sub.2 CH.sub.3                                                                H  H  CH CH.sub.3                                                                            OCH.sub.3                               H            NO.sub.2    H  H  CH CH.sub.3                                                                            OCH.sub.3                               H            CO.sub.2 CH.sub.3                                                                          H  H  CH CH.sub.3                                                                            OCH.sub.3                               H            CO.sub.2 CH.sub.2 CH.sub.3                                                                 H  H  CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     CO.sub.2 CH(CH.sub.3 ).sub.2                                                               H  H  CH CH.sub.3                                                                            OCH.sub.3                               H            Cl          H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           Cl          H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           OCH.sub.3   H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           NO.sub.2    H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           CH.sub.3    H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  CH CH.sub.3                                                                            CH.sub.3                                CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  CH Cl   OCH.sub.3                               CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  CH Cl   NH.sub.2                                CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  N  OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  N  CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  N  CH.sub.3                                                                            CH.sub.3                                CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  N  OCH.sub.3                                                                           NHCH.sub.3                              CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub. 2                      CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  CH CH.sub.3                                                                            CH.sub.3                                CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  CH Cl   OCH.sub.3                               CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  CH Cl   NH.sub.2                                CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  N  OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  N  CH.sub.3                                                                            OCH.sub.3                               CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  N  CH.sub.3                                                                            CH.sub.3                                CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  N  CH.sub.3 O                                                                          NHCH.sub.3                              CH.sub.3     SO.sub.2 N(CH.sub.3).sub.2                                                                 H  H  N  CH.sub.3 O                                                                          N(CH.sub.3).sub.2                       CH.sub.3     SO.sub.2 CH.sub.3                                                                          H  H  CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3     SO.sub.2 CH.sub.3                                                                          H  H  CH Cl   OCH.sub.3                               CH.sub.3     SO.sub.2 CH.sub.3                                                                          H  H  N  OCH.sub.3                                                                           NHCH.sub.3                              CH.sub.3     SO.sub.2 CH.sub.3                                                                          H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                       CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  CH CH.sub.3                                                                            OCH.sub.2 CH.sub.3                      CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  CH CH.sub.3                                                                            CH.sub.2 OCH.sub.3                      CH.sub.3     CO.sub.2 CH.sub.3                                                                          H  H  CH CH.sub.3                                                                            CH.sub.2 (OCH.sub.3).sub.2              CH.sub.3 CH.sub.2                                                                           CO.sub.2 CH.sub.3                                                                          H  CH.sub.3                                                                          CH CH.sub.3                                                                            OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           CO.sub.2 CH.sub.3                                                                          H  CH.sub.3                                                                          CH CH.sub.3                                                                            CH.sub.3                                CH.sub.3 CH.sub.2                                                                           CO.sub.2 CH.sub.3                                                                          H  CH.sub.3                                                                          CH OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           CO.sub.2 CH.sub.3                                                                          H  CH.sub.3                                                                          N  OCH.sub.3                                                                           OCH.sub.3                               CH.sub.3 CH.sub.2                                                                           CO.sub.2 CH.sub.3                                                                          H  CH.sub.3                                                                          N  OCH.sub.3                                                                           CH.sub.3                                CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         CH.sub.3                                CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCH.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         CH.sub.3                                CH.sub.2 CH.sub.3                                                                           H           H  H  CH SCF.sub.2 H                                                                         CH.sub.3                                CH.sub.2 CH.sub.3                                                                           H           H  H  CH SCF.sub.2 H                                                                         OCH.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  CH SCF.sub.2 H                                                                         OCF.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCH.sub.3                                                                           OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCF.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCH.sub.3                                                                           OCF.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            OCF.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCF.sub.2 CHClF                         CH.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCHF.sub.3                                                                          OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCH.sub.3                                                                           OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub. 3                                                                          H           H  H  CH OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                       CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CH.sub.3                      CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                      CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         CH(OCH.sub.3).sub.2                     CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCF.sub.3                               CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         NH.sub.2                                CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         NHCH.sub.3                              CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                       CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 H                             CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHClF                         CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                         CH.sub.2 CH.sub.3                                                                           H           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub. 3                                                                          H           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub.3                                                                           H           H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                    CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                       CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                      CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                      CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         NH.sub.2                                CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                       CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                         CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                   CH.sub.2 CH.sub.3                                                                           H           H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 H                             CH.sub.2 CH.sub.3                                                                           H           H  H  N  CH.sub.3                                                                            OCF.sub.2 H                             __________________________________________________________________________

                  TABLE IVb                                                        ______________________________________                                          ##STR131##                                                                    R.sub.10                                                                               R.sub.11                                                                              R.sub.12                                                                              R    A    Y'      m.p. (°C.)                      ______________________________________                                         CH.sub.2 CH.sub.3                                                                      H      H      H    A-2  H                                              CH.sub.2 CH.sub.3                                                                      H      H      H    A-2  Cl                                             CH.sub.2 CH.sub.3                                                                      H      H      H    A-2  CH.sub.3                                       CH.sub.2 CH.sub.3                                                                      H      H      H    A-2  OCH.sub.3                                      CH.sub.2 CH.sub.3                                                                      H      H      H    A-2  OCF.sub.2 H                                    CH.sub.2 CH.sub.3                                                                      H      H      H    A-3  H                                              CH.sub.2 CH.sub.3                                                                      H      H      H    A-3  Cl                                             CH.sub.2 CH.sub.3                                                                      H      H      H    A-3  CH.sub.3                                       CH.sub.2 CH.sub.3                                                                      H      H      H    A-3  OCH.sub.3                                      CH.sub.2 CH.sub.3                                                                      H      H      H    A-3  OCF.sub.2 H                                    CH.sub.2 CH.sub.3                                                                      H      H      H    A-4  H                                              CH.sub.2 CH.sub.3                                                                      H      H      H    A-4  Cl                                             CH.sub.2 CH.sub.3                                                                      H      H      H    A-4  CH.sub.3                                       CH.sub.2 CH.sub.3                                                                      H      H      H    A-4  OCH.sub.3                                      CH.sub.2 CH.sub.3                                                                      H      H      H    A-4  OCF.sub.2 H                                    ______________________________________                                    

                                      TABLE IVc                                    __________________________________________________________________________      ##STR132##                                                                    R.sub.10                                                                             R.sub.11                                                                          R.sub.12                                                                          R  A  X.sup.2                                                                              Y.sup.2                                                                             X.sup.3                                                                            m.p. (°C.)                             __________________________________________________________________________     CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.3                                                                            --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.2 CF.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.3                                                                            --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.2 CF.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                            --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.2 CH.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.2 CF.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.3                                                                            --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.2 CF.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                            --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.2 CH.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.2 CF.sub.3                                                                   --                                                CH.sub.2 CH.sub.3                                                                    H  H  H  A-6                                                                               --    --   OCH.sub.3                                         CH.sub.2 CH.sub.3                                                                    H  H  H  A-6                                                                               --    --   CH.sub.3                                          __________________________________________________________________________

                                      TABLE Va                                     __________________________________________________________________________      ##STR133##                                                                    R.sub.11     R.sub.12                                                                          R  Z  X    Y       m.p. (°C.)                           __________________________________________________________________________     H            H  H  CH CH.sub.3                                                                            OCH.sub.3                                           CH.sub.3     H  H  CH OCH.sub.3                                                                           OCH.sub.3                                           CH.sub.3 CH.sub.2                                                                           H  H  CH CH.sub.3                                                                            CH.sub.3                                            CH.sub.3 CH.sub.2 CH.sub.2                                                                  H  H  CH Cl   OCH.sub.3                                           (CH.sub.3).sub.2 CH                                                                         H  H  N  CH.sub.3                                                                            OCH.sub.3                                           F            H  H  N  CH.sub.3                                                                            OCH.sub.3                                           Cl           H  H  N  OCH.sub.3                                                                           OCH.sub.3                                           Br           H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                                   NO.sub.2     H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                                   OCH.sub.3    H  H  CH CH.sub.3                                                                            OCH.sub.3                                           OCH.sub.2 CH.sub.3                                                                          H  H  N  CH.sub.3                                                                            OCH.sub.3                                           OCH.sub.2 CH.sub.2 CH.sub.3                                                                 H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                                   OCH(CH.sub.3).sub.2                                                                         H  H  CH Cl   OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH OCH.sub.3                                                                           OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.3                                                                  H  H  CH CH.sub.3                                                                            OCH.sub.3                                           CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         H  H  CH CH.sub.3                                                                            CH.sub.3                                            CO.sub.2 CH(CH.sub.3).sub.2                                                                 H  H  CH OCH.sub.3                                                                           OCH.sub.3                                           CO.sub.2 CH.sub.2 CHCH.sub.2                                                                H  H  CH CH.sub.3                                                                            OCH.sub.3                                           SCH.sub.3    H  H  N  OCH.sub.3                                                                           OCH.sub.3                                           SCH.sub.2 CH.sub.3                                                                          H  H  N  OCH.sub.3                                                                           OCH.sub.3                                           SCH.sub.2 CH.sub.2 CH.sub.3                                                                 H  H  N  OCH.sub.3                                                                           OCH.sub.3                                           SOCH.sub.3   H  H  N  OCH.sub.3                                                                           OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  CH.sub.3                                                                          CH CH.sub.3                                                                            OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  CH.sub.3                                                                          CH CH.sub.3                                                                            CH.sub.3                                            CO.sub.2 CH.sub.3                                                                           H  CH.sub.3                                                                          CH OCH.sub.3                                                                           OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  CH.sub.3                                                                          N  OCH.sub.3                                                                           OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  CH.sub.3                                                                          N  CH.sub.3                                                                            OCH.sub.3                                           SO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCH.sub.2 CH.sub.3                                  SO.sub.2 CH.sub.3                                                                           H  H  N  OCH.sub.3                                                                           NH.sub.2                                            SO.sub.2 CH.sub.3                                                                           H  H  N  OCH.sub.3                                                                           NHCH.sub.3                                          SO.sub.2 CH.sub.3                                                                           H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                                   SO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            CH.sub.2 OCH.sub.3                                  SO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                 SO.sub.2 CH.sub.3                                                                           H  H  CH OCH.sub.3                                                                           OCH.sub.3                                           SO.sub.2 CH.sub.2 CH.sub.3                                                                  H  H  CH OCH.sub.3                                                                           CH.sub.3                                            SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                         H  H  N  OCH.sub.3                                                                           OCH.sub.3                                           SO.sub.2 N(CH.sub.3).sub.2                                                                  H  H  N  CH.sub.3                                                                            OCH.sub.3                                           SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                     H  H  N  OCH.sub.3                                                                           N(CH.sub.3).sub.2                                   SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                         H  H  N  OCH.sub.3                                                                           CH.sub.3                                            CO.sub.2 CH.sub.3                                                                           CH.sub.3                                                                          H  CH CH.sub.3                                                                            OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            CH.sub.3                                            CO.sub.2 CH.sub.3                                                                           H  H  CH OCH.sub.3                                                                           OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  N  CH.sub.3                                                                            OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  N  OCH.sub.3                                                                           OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         CH.sub.3                                            CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         CH.sub.3                                            CO.sub.2 CH.sub.3                                                                           H  H  CH SCF.sub.2 H                                                                         CH.sub.3                                            CO.sub.2 CH.sub.3                                                                           H  H  CH SCF.sub.2 H                                                                         OCH.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH SCF.sub.2 H                                                                         OCF.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCH.sub.2 CF.sub.3                                  CO.sub.2 CH.sub.3                                                                           H  H  CH OCH.sub.3                                                                           OCH.sub.2 CF.sub.3                                  CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCF.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH OCH.sub.3                                                                           OCF.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  N  CH.sub.3                                                                            OCF.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCF.sub.2 CHClF                                     CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                                CO.sub.2 CH.sub.3                                                                           H  H  CH OCH.sub.3                                                                           OCF.sub.2 CF.sub.2 H                                CO.sub.2 CH.sub.3                                                                           H  H  N  CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                                CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCF.sub.2 CHFCF.sub.3                               CO.sub.2 CH.sub.3                                                                           H  H  CH OCH.sub.3                                                                           OCF.sub.2 CHFCF.sub.3                               CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CH.sub.3                                  CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         CH(OCH.sub.3).sub.2                                 CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                                  CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCF.sub.3                                           CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         NH.sub.2                                            CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         NHCH.sub.3                                          CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                                   CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 H                                         CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHClF                                     CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                                     CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CF.sub.2 H                                CO.sub.2 CH.sub.3                                                                           H  H  CH OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                               CO.sub.2 CH.sub.3                                                                           H  H  CH CH.sub.3                                                                            OCF.sub.2 CF.sub.2 H                                CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         CH.sub.2 CH.sub.3                                   CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         CH.sub.2 OCH.sub.3                                  CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         OCH.sub.2 CF.sub.3                                  CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         NH.sub.2                                            CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         N(CH.sub.3).sub.2                                   CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHBrF                                     CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 CHFCF.sub.3                               CO.sub.2 CH.sub.3                                                                           H  H  N  OCF.sub.2 H                                                                         OCF.sub.2 H                                         CO.sub.2 CH.sub.3                                                                           H  H  N  CH.sub.3                                                                            OCF.sub.2 H                                         __________________________________________________________________________

                  TABLE Vb                                                         ______________________________________                                          ##STR134##                                                                    R.sub.11  R.sub.12                                                                               R      A     Y'      m.p.(°C.)                        ______________________________________                                         CO.sub.2 CH.sub.3                                                                        H       H      A-2   H                                               CO.sub.2 CH.sub.3                                                                        H       H      A-2   Cl                                              CO.sub.2 CH.sub.3                                                                        H       H      A-2   CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       H      A-2   OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       H      A-2   OCF.sub.2 H                                     CO.sub.2 CH.sub.3                                                                        H       H      A-3   H                                               CO.sub.2 CH.sub.3                                                                        H       H      A-3   Cl                                              CO.sub.2 CH.sub.3                                                                        H       H      A-3   CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       H      A-3   OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       H      A-3   OCF.sub.2 H                                     CO.sub.2 CH.sub.3                                                                        H       H      A-4   H                                               CO.sub.2 CH.sub.3                                                                        H       H      A-4   Cl                                              CO.sub.2 CH.sub.3                                                                        H       H      A-4   CH.sub.3                                        CO.sub.2 CH.sub.3                                                                        H       H      A-4   OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                        H       H      A-4   OCF.sub.2 H                                     ______________________________________                                    

                  TABLE Vc                                                         ______________________________________                                          ##STR135##                                                                                                                  m.p.                             R.sub.11                                                                               R.sub.12                                                                              R     A    X.sup.2                                                                              Y.sup.2  X.sup.3                                                                             (°C.)                     ______________________________________                                         CO.sub.2 CH.sub.3                                                                      H      H     A-5  OCH.sub.3                                                                             CH.sub.3                                                                               --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  OCH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  OCH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  CH.sub.3                                                                              CH.sub.3                                                                               --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  CH.sub.3                                                                              CH.sub.2 CH.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  CH.sub.3                                                                              CH.sub.2 CF.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  CH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                               --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  CH.sub.2 CH.sub. 3                                                                    CH.sub.2 CH.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  CH.sub.2 CH.sub.3                                                                     CH.sub.2 CF.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  OCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                               --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  OCH.sub.2 CH.sub.3                                                                    CH.sub.2 CF.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  SCH.sub.3                                                                             CH.sub.3                                                                               --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  SCH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  SCH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  SCH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                               --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  SCH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-5  SCH.sub.2 CH.sub.3                                                                    CH.sub.2 CF.sub.3                                                                      --                                    CO.sub.2 CH.sub.3                                                                      H      H     A-6  --     --      OCH.sub.3                             CO.sub.2 CH.sub.3                                                                      H      H     A-6  --     --      CH.sub.3                              ______________________________________                                    

                                      TABLE VIa                                    __________________________________________________________________________      ##STR136##                                                                    R.sub.13       R.sub.14    R.sub.15                                                                            R    Z    X      Y  m.p.(°C.)           __________________________________________________________________________     H              H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CH.sub.3       H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CH.sub.3 CH.sub.2                                                                             CH.sub.3    H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CH.sub.3 CH.sub.2 CH.sub.2                                                                    H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     (CH.sub.3).sub.2 CH                                                                           CH.sub.3    H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CH.sub.3 O     H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CH.sub.3 CH.sub.2 O                                                                           CH.sub.3    H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CH.sub.3 CH.sub.2 CH.sub. 2 O                                                                 H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     F              H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     Cl             H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     Br             H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     NO.sub.2       H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.2 CH.sub.3                                                                    H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.2 CHCH.sub.2                                                                  H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SCH.sub.3      H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SCH.sub.2 CH.sub.3                                                                            H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SCH.sub.2 CH.sub.2 CH.sub.3                                                                   H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SOCH.sub.3     H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SO.sub.2 CH.sub.2 CH.sub.3                                                                    H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                           H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SO.sub.2 N(CH.sub.3)(CH.sub.2 CH.sub.3)                                                       H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                           H           H    H    CH   CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCH.sub.3                                                                             OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              CH.sub.3                      CO.sub.2 CH.sub.3                                                                             H           H    H    CH   Cl     OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   Cl     NH.sub.2                      CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCH.sub.3                                                                             OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCH.sub.3                                                                             CH.sub.3                      CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCH.sub.3                                                                             NHCH.sub.3                    CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCH.sub.3                                                                             N(CH.sub.3).sub.2             SO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCH.sub.3                                                                             OCH.sub.3                     SO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              CH.sub.3                      SO.sub.2 CH.sub.3                                                                             H           H    H    CH   Cl     OCH.sub.3                     SO.sub. 2 CH.sub.3                                                                            H           H    H    CH   Cl     NH.sub.2                      SO.sub.2 CH.sub.3                                                                             H           H    H    N    CH.sub.3                                                                              CH.sub.3                      SO.sub.2 CH.sub.3                                                                             H           H    H    N    OCH.sub.3                                                                             OCH.sub.3                     SO.sub.2 CH.sub.3                                                                             H           H    H    N    CH.sub.3                                                                              OCH.sub.3                     SO.sub.2 CH.sub.3                                                                             H           H    H    N    OCH.sub.3                                                                             NH.sub.2                      SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    CH   OCH.sub.3                                                                             OCH.sub.3                     SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    CH   CH.sub.3                                                                              CH.sub.3                      SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    CH   Cl     OCH.sub.3                     SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    CH   Cl     NH.sub.2                      SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    N    CH.sub.3 O                                                                            NHCH.sub.3                    SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    N    CH.sub.3 O                                                                            N(CH.sub.3).sub.2             SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    N    CH.sub.3 O                                                                            CH.sub.3 O                    SO.sub.2 N(CH.sub.3).sub.2                                                                    H           H    H    N    CH.sub.3                                                                              OCH.sub.3                     CH.sub.3       H           CH.sub.3                                                                            H    CH   CH.sub.3                                                                              OCH.sub.3                     CH.sub. 3 CH.sub.2                                                                            H           CH.sub.3                                                                            H    N    CH.sub.3                                                                              OCH.sub.3                     CH.sub.3       CH.sub.3    H    H    N    CH.sub.3                                                                              OCH.sub.3                     CH.sub.3       Cl          H    H    N    CH.sub.3                                                                              OCH.sub.3                     Cl             Cl          H    H    N    CH.sub.3                                                                              OCH.sub.3                     NO.sub.2       Cl          H    H    N    CH.sub.3                                                                              OCH.sub.3                     H              CH.sub.3    CH.sub.3                                                                            H    CH   CH.sub.3                                                                              OCH.sub.3                     H              CH.sub.3 CH.sub.2                                                                          CH.sub.3                                                                            H    CH   CH.sub.3                                                                              OCH.sub.3                     H              CH.sub.3 CH.sub.2 CH.sub.2                                                                 CH.sub.3                                                                            H    CH   CH.sub.3                                                                              OCH.sub.3                     H              (CH.sub.3).sub.2 CH                                                                        CH.sub.3                                                                            H    CH   CH.sub.3 OCH.sub.3                   H              OCH.sub.3   CH.sub.3                                                                            H    CH   CH.sub.3 OCH.sub.3                   H              OCH.sub.2 CH.sub.3                                                                         CH.sub.3                                                                            H    CH   CH.sub.3                                                                              OCH.sub.3                     H              OCH.sub.2 CH.sub.2 CH.sub.3                                                                CH.sub.3                                                                            H    CH   OCH.sub.3                                                                             OCH.sub.3                     H              F           CH.sub.3                                                                            H    CH   CH.sub.3                                                                              CH.sub.3                      H              Cl          CH.sub.3                                                                            H    CH   CH.sub.3                                                                              OCH.sub.3                     H              Br          CH.sub.3                                                                            H    CH   OCH.sub.3                                                                             OCH.sub.3                     H              NO.sub.2    CH.sub.3                                                                            H    CH   CH.sub.3                                                                              CH.sub.3                      H              CO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                            H    CH   OCH.sub.3                                                                             OCH.sub.3                     H              CO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                            H    CH   OCH.sub.3                                                                             CH.sub.3                      H              SO.sub.2 CH.sub.3                                                                          CH.sub.3                                                                            N    OCH.sub.3                                                                           OCH.sub.3                            H              SO.sub.2 CH.sub.2 CH.sub.3                                                                 CH.sub.3                                                                            H    N    CH.sub.3                                                                              OCH.sub.3                     H              SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                        CH.sub.3                                                                            H    N    CH.sub.3                                                                              OCH.sub.3                     H              SO.sub.2 N(CH.sub.3).sub.2                                                                 CH.sub.3                                                                            H    N    CH.sub.3                                                                              OCH.sub.3                     H              SO.sub.2 (CH.sub.3)                                                                        CH.sub.3                                                                            H    N    CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    CH.sub.3                                                                            CH   CH.sub.3                                                                              CH.sub.3                      CO.sub.2 CH.sub.3                                                                             H           H    CH.sub.3                                                                            CH   CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    CH.sub.3                                                                            CH   OCH.sub.3                                                                             OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    CH.sub.3                                                                            N    OCH.sub.3                                                                             OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    CH.sub.3                                                                            N    OCH.sub.3                                                                             N(CH.sub.3).sub.2             CO.sub.2 CH.sub.3                                                                             H           H    CH.sub.3                                                                            N    CH.sub.3                                                                              OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    CH.sub.3                                                                            N    CH.sub.3                                                                              CH.sub. 3                     SO.sub.2 CH.sub.3                                                                             H           H    H    CH   Cl     NH.sub.2                      SO.sub.2 CH.sub.3                                                                             H           H    CH   Cl   NHCH.sub.3                           SO.sub.2 CH.sub.3                                                                             H           H    N    CH.sub.3                                                                            OCH.sub.2 CH.sub.3                   SO.sub.2 CH.sub.3                                                                             H           H    N    CH.sub.3                                                                            CH.sub.2 OCH.sub.3                   SO.sub.2 CH.sub.3                                                                             H           H    N    CH.sub.3                                                                            CH(OCH.sub.3).sub.2                  CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           CH.sub.3                      CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           CH.sub.3                      CO.sub.2 CH.sub.3                                                                             H           H    H    CH   SCF.sub.2 H                                                                           CH.sub.3                      CO.sub.2 CH.sub.3                                                                             H           H    H    CH   SCF.sub.2 H                                                                           OCH.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   SCF.sub.2 H                                                                           OCF.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCH.sub.2 CF.sub.3            CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCH.sub.3                                                                             OCH.sub.2 CF.sub.3            CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCF.sub.3                     CO.sub. 2 CH.sub.3                                                                            H           H    H    CH   OCH.sub.3                                                                             OCF.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    N    CH.sub.3                                                                              OCF.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCF.sub.2 CHClF               CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCF.sub.2 CF.sub.2 H          CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCH.sub.3                                                                             OCF.sub.2 CF.sub.2 H          CO.sub.2 CH.sub.3                                                                             H           H    H    N    CH.sub.3                                                                              OCF.sub.2 CF.sub.2 H          CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCF.sub.2 CHFCF.sub.3         CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCH.sub.3                                                                             OCF.sub.2 CHFCF.sub.3         CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           CH.sub.2 CH.sub.3             CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCH.sub.2 CH.sub.3            CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           CH.sub.2 OCH.sub.3            CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           CH(OCH.sub.3).sub.2           CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCH.sub.2 CF.sub.3            CO.sub.2 CH.sub. 3                                                                            H           H    H    CH   OCF.sub.2 H                                                                           OCF.sub.3                     CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           NH.sub.2                      CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           NHCH.sub.3                    CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           N(CH.sub.3).sub.2             CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCF.sub.2 H                   CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCF.sub.2 CHClF               CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCF.sub.2 CHBrF               CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCF.sub.2 CF.sub.2 H          CO.sub.2 CH.sub.3                                                                             H           H    H    CH   OCF.sub.2 H                                                                           OCF.sub.2 CHFCF.sub.3         CO.sub.2 CH.sub.3                                                                             H           H    H    CH   CH.sub.3                                                                              OCF.sub.2 CF.sub.2 H          CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           CH.sub.2 CH.sub.3             CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           CH.sub.2 OCH.sub.3            CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           OCH.sub.2 CF.sub.3            CO.sub.2 CH.sub. 3                                                                            H           H    H    N    OCF.sub.2 H                                                                           NH.sub.2                      CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           N(CH.sub.3).sub.2             CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           OCF.sub.2 CHBrF               CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           OCF.sub.2 CHFCF.sub.3         CO.sub.2 CH.sub.3                                                                             H           H    H    N    OCF.sub.2 H                                                                           OCF.sub.2 H                   CO.sub.2 CH.sub.3                                                                             H           H    H    N    CH.sub.3                                                                              OCF.sub.2 H                   H              CH.sub.3    CH.sub.3                                                                            H    CH   OCH.sub.3                                                                             OCH.sub.3                                                                              207-210°       H              CH.sub.3    CH.sub.3                                                                            H    CH   CH.sub.3                                                                              CH.sub.3                                                                               204-208°       H              CH.sub.3    CH.sub.3                                                                            H    N    CH.sub.3                                                                              OCH.sub.3                                                                              197-201°       H              CH.sub.3    CH.sub.3                                                                            H    N    OCH.sub.3                                                                             OCH.sub.3                                                                              174-179°       H              CH.sub.3    CH.sub.3                                                                            H    N    CH.sub.3                                                                              CH.sub.3                                                                               211-215°       CH.sub.3       H           CH.sub.3                                                                            H    CH   OCH.sub.3                                                                             OCH.sub.3                                                                              189-191°       CH.sub.3       H           CH.sub.3                                                                            H    CH   CH.sub.3                                                                              CH.sub.3                                                                               210-215°       CH.sub.3       H           CH.sub.3                                                                            H    N    CH.sub. 3                                                                             OCH.sub.3                                                                              183-186°       CH.sub.3       H           CH.sub.3                                                                            H    N    OCH.sub.3                                                                             OCH.sub.3                                                                              187-189°       CH.sub.3       H           CH.sub.3                                                                            H    N    CH.sub.3                                                                              CH.sub.3                                                                               225-226°       __________________________________________________________________________

                  TABLE VIb                                                        ______________________________________                                          ##STR137##                                                                    R.sub.13                                                                              R.sub.14                                                                               R.sub.15                                                                               R    A     Y'     m.p.                                  ______________________________________                                         CO.sub.2 CH.sub.3                                                                     H       H       H    A-2   H                                            CO.sub.2 CH.sub.3                                                                     H       H       H    A-2   Cl                                           CO.sub.2 CH.sub.3                                                                     H       H       H    A-2   CH.sub.3                                     CO.sub.2 CH.sub.3                                                                     H       H       H    A-2   OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                     H       H       H    A-2   OCF.sub.2 H                                  CO.sub.2 CH.sub.3                                                                     H       H       H    A-3   H                                            CO.sub.2 CH.sub.3                                                                     H       H       H    A-3   Cl                                           CO.sub.2 CH.sub.3                                                                     H       H       H    A-3   CH.sub.3                                     CO.sub.2 CH.sub.3                                                                     H       H       H    A-3   OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                     H       H       H    A-3   OCF.sub.2 H                                  CO.sub.2 CH.sub.3                                                                     H       H       H    A-4   H                                            CO.sub.2 CH.sub.3                                                                     H       H       H    A-4   Cl                                           CO.sub.2 CH.sub.3                                                                     H       H       H    A-4   CH.sub.3                                     CO.sub.2 CH.sub.3                                                                     H       H       H    A-4   OCH.sub.3                                    CO.sub.2 CH.sub.3                                                                     H       H       H    A-4   OCF.sub.2 H                                  ______________________________________                                    

                                      TABLE VIc                                    __________________________________________________________________________      ##STR138##                                                                    R.sub.13                                                                             R.sub.14                                                                          R.sub.15                                                                          R  A  X.sup.2                                                                              Y.sup.2                                                                             X.sup.3                                                                            m.p.(°C.)                              __________________________________________________________________________     CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.3                                                                            --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.2 CF.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.3                                                                            CH.sub.2 CF.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.3                                                                            --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.3                                                                             CH.sub.2 CF.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.3                                                                            --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.2 CH.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               CH.sub.2 CH.sub.3                                                                    CH.sub.2 CF.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                            --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.2 CH.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               OCH.sub.2 CH.sub.3                                                                   CH.sub.2 CF.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.3                                                                            --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.2 CH.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.3                                                                            CH.sub.2 CF.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                            --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.2 CH.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-5                                                                               SCH.sub.2 CH.sub.3                                                                   CH.sub.2 CF.sub.3                                                                   --                                                CO.sub.2 CH.sub.3                                                                    H  H  H  A-6                                                                               --    --   OCH.sub.3                                         CO.sub.2 CH.sub.3                                                                    H  H  H  A-6                                                                               --    --   CH.sub.3                                          __________________________________________________________________________

Formulations

Useful formulations of the compounds of Formula I can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates and the like. Many of these may be applied directly. Sprayable formulations can be extended in suitable media and used at spray volumes of from a few liters to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations, broadly, contain about 0.1% to 99% by weight of active ingredient(s) and at least one of (a) about 0.1% to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). More specifically, they will contain these ingredients in the following approximate proportions:

                  TABLE VII                                                        ______________________________________                                                     Active  Weight Percent*                                                        Ingredient                                                                             Diluent(s)                                                                               Surfactant(s)                                    ______________________________________                                         Wettable Powders                                                                             20-90      0-74     1-10                                         Oil Suspensions,                                                                              3-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Aqueous Suspension                                                                           10-50     40-84     1-20                                         Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.1-95      5-99.9  0-15                                         High Strength 90-99      0-10     0-2                                          Compositions                                                                   ______________________________________                                          *Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be present depending on the intended use and the physical properties of the compound. Higher ratios of surfactant to active ingredient are sometimes desirable, and are achieved by incorporation into the formulation or by tank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books, Caldwell, N.J., but other solids, either mined or manufactured, may be used. The more absorptive diluents are preferred for wettable powders and the denser ones for dusts. Typical liquid diluents and solvents are described in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York, 1950. Solubility under 0.1% is preferred for suspension concentrates; solution concentrates are preferably stable against phase separation at 0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC Publishing Corp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia of Surface Active Agents", Chemical Publishing Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foaming, caking, corrosion, microbiological growth, etc.

The methods of making such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer or fluid energy mill. Suspensions are prepared by wet milling (see, for example, Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made by spraying the active material upon performed granular carriers or by agglomeration techniques. See J. E. Browning, "Agglomeration", Chemical Engineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see for example:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,822, Jun. 23, 1959, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwise indicated.

EXAMPLE 9 Wettable Powder

    ______________________________________                                         N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-                                                           80%                                                (1-methylethyl)-1H-imidazole-2-sulfonamide                                     sodium alkylnaphthalenesulfonate                                                                           2%                                                 sodium ligninsulfonate      2%                                                 synthetic amorphous silica  3%                                                 kaolinite                   13%                                                ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids are essentially under 50 microns, reblended, and packaged.

EXAMPLE 10 Wettable Powder

    ______________________________________                                         N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-                                                       50%                                              (1-methylethyl)-1H-imidazole-2-sulfonamide                                     sodium alkylnaphthalenesulfonate                                                                             2%                                               low viscosity methyl cellulose                                                                               2%                                               diatomaceous earth            46%                                              ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in diameter. The product is reblended before packaging.

EXAMPLE 11 Granule

    ______________________________________                                         Wettable Powder of Example 10                                                                            5%                                                   attapulgite granules      95%                                                  (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                              ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on the surface of attapulgite granules in a double-cone blender. The granules are dried and packaged.

EXAMPLE 12 Extruded Pellet

    ______________________________________                                         N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-                                                           25%                                               (1-methylethyl)-1H-imidazole-2-sulfonamide                                     anhydrous sodium sulfate     10%                                               crude calcium ligninsulfonate                                                                               5%                                                sodium alkylnaphthalenesulfonate                                                                            1%                                                calcium/magnesium bentonite  59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about 12% water. The mixture is extruded as cylinders about 3 mm diameter which are cut to produce pellets about 3 mm long. These may be used directly after drying, or the dried pellets may be crushed to pass a U.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S. No. 40 sieve (0.42 mm openings) may be packaged for use and the fines recycled.

EXAMPLE 13 Oil Suspension

    ______________________________________                                         N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-                                                           25%                                                ethyl-1H-imidazole-2-sulfonamide                                               polyoxyethylene sorbitol hexaoleate                                                                        5%                                                 highly aliphatic hydrocarbon oil                                                                           70%                                                ______________________________________                                    

The ingredients are ground together in a sand mill until the solid particles have been reduced to under about 5 microns. The resulting thick suspension may be applied directly, but preferably after being extended with oils or emulsified in water.

EXAMPLE 14 Wettable Powder

    ______________________________________                                         N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-                                                       20%                                              ethyl-1H-imidazole-2-sulfonamide                                               sodium alkylnaphthalenesulfonate                                                                             4%                                               sodium ligninsulfonate        4%                                               low viscosity methyl cellulose                                                                               3%                                               attapulgite                   69%                                              ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-mill to produce particles essentially all below 100 microns, the material is reblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) and packaged.

EXAMPLE 15 Low Strength Granule

    ______________________________________                                         N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-                                                          1%                                                 ethyl-1H-imidazole-2-sulfonamide                                               N,N-dimethylformamide       9%                                                 attapulgite granules        90%                                                (U.S.S. 20-40 sieve)                                                           ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution is sprayed upon dedusted granules in a double cone blender. After spraying of the solution has been completed, the blender is allowed to run for a short period and then the granules and packaged.

EXAMPLE 16 Aqueous Suspension

    ______________________________________                                         N-[(4,6-dimethylpyrimidin-2-yl)aminocabonyl]-1-                                                            40%                                                (1-methylethyl)-1H-imidazole-2-sulfonamide                                     polyacrylic acid thickener  0.3%                                               dodecylphenol polyethylene glyco1 ether                                                                    0.5%                                               disodium phospate           1%                                                 monosodium phosphate        0.5%                                               polyvinyl alcohol           1.0%                                               water                       56.7%                                              ______________________________________                                    

The ingredients are blended and ground together in a sand mill to produce particles essentially all under 5 microns in size.

EXAMPLE 17 Solution

    ______________________________________                                         N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-                                                        5%                                                1-(1-methylethyl)-1H-imidazole-2-sulfonamide,                                  sodium salt                                                                    water                        95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce the solution, which may then be packaged for use.

EXAMPLE 18 Low Strength Granule

    ______________________________________                                         N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-                                                          0.1%                                               (1-methylethyl)-1H-imidazole-2-sulfonamide                                     attapulgite granules        99.9%                                              (U.S.S. 20-40 mesh)                                                            ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution is sprayed upon dedusted granules in a double-cone blender. After spraying of the solution has been completed, the material is warmed to evaporate the solvent. The material is allowed to cool and then packaged.

EXAMPLE 19 Granule

    ______________________________________                                         N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-                                                            80%                                               ethyl-1H-imidazole-2-sulfonamide                                               wetting agent                1%                                                crude ligninsulfonate salt (containing                                                                      10%                                               5-20% of the natural sugars)                                                   attapulgite clay             9%                                                ______________________________________                                    

The ingredients are blended and milled to pass through a 100 mesh screen. This material is then added to a fluid bed granulator, the air flow is adjusted to gently fluidize the material, and a fine spray of water is sprayed onto the fluidized material. The fluidization and spraying are continued until granules of the desired size range are made. The spraying is stopped, but fluidization is continued, optionally with heat, until the water content is reduced to the desired level, generally less than 1%. The material is then discharged, screened to the desired size range, generally 14-100 mesh (1410-149 microns), and packaged for use.

EXAMPLE 20 High Strength Concentrate

    ______________________________________                                         N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-                                                       99%                                              ethyl-1H-imidazole-2-sulfonamide                                               silica aerogel                0.5%                                             synthetic amorphous silica    0.5%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce a material essentially all passing a U.S.S. No. 50 screen (0.3 mm opening). The concentrate may be formulated further if necessary.

EXAMPLE 21 Wettable Powder

    ______________________________________                                         N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-                                                          90%                                                ethyl-1H-imidazole-2-sulfonamide                                               dioctyl sodium sulfosuccinate                                                                              0.1%                                               synthetic fine silica       9.9%                                               ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce particles essentially all below 100 microns. The material is sifted through a U.S.S. No. 50 screen and then packaged.

EXAMPLE 22 Wettable Powder

    ______________________________________                                         N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-1-                                                         40%                                                  (1-methylethyl)-1H-imidazole-2-sulfonamide                                     sodium ligninsulfonate    20%                                                  montmorillonite clay      40%                                                  ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and then air-milled to produce particles essentially all below 10 microns in size. The material is reblended and the packaged.

EXAMPLE 23 Oil Suspension

    ______________________________________                                         N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1-                                                       35%                                              (1-methylethyl)-1H-imidazole-2-sulfonamide                                     blend of polyalcohol carboxylic                                                                              6%                                               esters and oil soluble petroleum                                               sulfonates                                                                     xylene                        59%                                              ______________________________________                                    

The ingredients are combined and ground together in a sand mill to produce particles essentially all below 5 microns. The product can be used directly, extended with oils, or emulsified in water.

Utility

Test results indicate that the compounds of the present invention are powerful herbicides. Many of them have utility for broad-spectrum pre- and/or post-emergence weed control in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, parking lots, drive-in theaters, around billboards, highway and railroad structures. Alternatively, the subject compounds should be useful to modify plant growth.

The rates of application for the compounds of the invention are determined by a number of factors, including their use as plant growth modifiers or as herbicides, the crop species involved, the types of weeds to be controlled, weather and climate, formulations selected, mode of application, amount of foliage present, etc. In general terms, the subject compounds should be applied at levels of around 0.02 to 10 kg/ha, the lower rates being suggested for use on lighter soils and/or those havingg a low organic matter content, for plant growth modification or for situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any other commercial herbicide, examples of which are those of the triazine, triazole, uracil, urea, amide, diphenylether, carbamate and bipyridylium types.

The herbicidal properties of the subject compounds were discovered in a number of greenhouse tests. The test procedures and results follow.

Although some of the compounds do not ehibit a high degree of activity at the rate tested, it is expected that these compounds will exhibit herbicidal effects at higher rates.

TEST A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia), morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn, soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were planted in a growth medium and treated pre-emergence with the chemicals dissolved in a nonphytotoxic solvent. At the same time, cotton having five leaves (including cotyledonary ones), bush beans with the third trifoliolate leaf expanding, crabgrass, barnyardgrass and wild oats with two leaves, sicklepod with three leaves (including cotyledonary ones), morningglory and cocklebur with four leaves (including the cotyledonary ones), sorghum and corn with four leaves, soybean with two cotyledonary leaves, rice with three leaves, wheat with one leaf, and nutsedge with three to five leaves were sprayed. Treated plants and controls were maintained in a greenhouse for sixteen days, whereupon all species were compared to controls and visually rated for response to treatment. The ratings are based on a numerical scale extending from 0=no injury, to 10=complete kill. The accompanying descriptive symbols have the following meanings:

C=chlorosis/necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

U=unusual pigmentation;

X=axillary stimulation; and

6Y=abscised buds or flowers.

The ratings for the compounds tested by this producere are presented in Table A. It will be seen that, at the low rates of application selected for this test, the compounds tested have utility for plant growth modification, and also are highly active herbicides. ##STR139##

                                      TABLE A                                      __________________________________________________________________________             Cmpd. 1                                                                              Cmpd. 2                                                                              Cmpd. 3                                                                              Cmpd. 4                                                                              Cmpd. 5                                                                              Cmpd. 6                                                                              Cmpd. 7                                                                              Cmpd. 8                      Rate kg/ha                                                                             0.4   0.4   0.4   0.4   0.05  0.05  0.05  0.05                         __________________________________________________________________________     POST-EMERGENCE                                                                 Bush bean                                                                              9C    5C,6G,6Y                                                                             9C    0     9C    9C    9C    1C                           Cotton  2U,4C,9G                                                                             5C,8G 5C,9G 0     4C,9G 5C,9G 5C,9G 0                            Morningglory                                                                           6C,9G 4C,9H 9C    0     5C,9G 9C    9C    0                            Cocklebur                                                                              9C    2C,8G 10C   0     5C,9G 9C    9C    0                            Sicklepod                                                                              5C,9G 2C    5C,8G 0     5C,9G 9C    9C    0                            Nutsedge                                                                               2C,9G 2C,8G 4C,9G 0     4C,9G 6C,9G 9C    0                            Crabgrass                                                                              2C,8G 2C,7G 2C,8G 0     2C,9G 6C,9G 9C    0                            Barnyardgrass                                                                          9C    3C,9H 9C    2G    10C   9C    9C    0                            Wild Oats                                                                              3C,9G 2C,9H 9G,5X 3G    5C,9G 5C,9G 2C,9G 0                            Wheat   2C,9G 2C,9G 6G    2G    3U,9G 2U,9G 3C,9G 0                            Corn    4U,9G 1C,5G 7U,9G 0     3U,9G 5U,9C 4U,9G 0                            Soybean 6C,9G 1C,4G 6C,9G 0     9C    9C    9C    0                            Rice    6C,9G 5C,9G 6C,9G 2C,6G 2U,9G 4C,9G 5C,9G 0                            Sorghum 4U,9G 3U,9G 2U,9G 0     9C    5U,9C 3U,9C 0                            PRE-EMERGENCE                                                                  Morningglory                                                                           9C    9G    10C   0     9G    9C    9C     5G                          Cocklebur                                                                              9H    9H    9H    0     9H    9H    9H    0                            Sicklepod                                                                              2C,9G 2C,4G 9G    0     2C,9G 5C,9G 5C,9G 2G                           Nutsedge                                                                               10E   2C,7G 10E   0     10E   10E   10E   0                            Crabgrass                                                                              9G,5C 2C,7G 2C,7G 0     3C,8G 3C,8G 3C,8G 0                            Barnyardgrass                                                                          5C,9H 5C,9H 5C,9H 0     4C,9H 6C,9H 5C,9H 2C                           Wild Oats                                                                              5C,9H 3C,8G 5C,9H 0     5C,9H 6C,9H 5C,9H 0                            Wheat   3C,9H 2C,9H 2C,9H 2G    9H    10E   9H    0                            Corn    5C,9G 2C,8H 9G    3G    9G    10E   10E   2C                           Soybean 9H    2C    9H    0     9H    9H    9H    0                            Rice    10E   9H    10E   9H    10E   10E   10E   3C,4G                        Sorghum 5C,9H 2C,9H 10H   0     5C,9H 7C,9H 5C,9H 3G                           __________________________________________________________________________             Cmpd. 9                                                                              Cmpd. 10                                                                             Cmpd. 11                                                                             Cmpd. 12                                                                             Cmpd. 13                                                                             Cmpd. 14                                                                             Cmpd. 15                                                                             Cmpd. 16                     Rate kg/ha                                                                             0.05  0.05  0.05  0.05  0.05  0.05  0.05  0.4                          __________________________________________________________________________     POST-EMERGENCE                                                                 Bush bean                                                                              3C,9G,6Y                                                                             9C    9C    9C    5C,9G,6Y                                                                             2C,2H 9C    0                            Cotton  1C    6C,9G 5C,9G 5C,9G 2C,8G 2C,5G 2C,5G 0                            Morningglory                                                                           1C,3G 4C,9G 9C    5C,9G 2C    2C    2C,8G 0                            Cocklebur                                                                              1C,5H 5C,9G 10C   10C   1H    1C    3C,9H 0                            Sicklepod                                                                              1C    2C,6G 7G    2C,8G 1C    0     2C,5G 0                            Nutsedge                                                                               0     2C,7G 2C,7G 2C,8G 0     0     2G    0                            Crabgrass                                                                              0     1C,5G 2C,4H 2C,5G 0     0     0     0                            Barnyardgrass                                                                          2C,3H 6C,9H 5C,9H 5C,9H 1H    0     2C,7H 0                            Wild Oats                                                                              2C,5G 5C,9G 5C,9H 2C,9G 0     0     2G    0                            Wheat   0     8G    7G    9G    0     0     0     0                            Corn    2C,8H 2U,9G 2U,9H 5U,9C 0     0     2C,5G 0                            Soybean 0     5C,9G 4C,9H 9C    1C,5H 0     3C,9H 0                            Rice    4C,9G 6C,9G 5C,9G 6C,9G 4C,9G 3G    7G    5G                           Sorghum 4C,9H 6C,9G 4U,9G 10C   3C,9H 2G    3C,9H 1C,3H                        PRE-EMERGENCE                                                                  Morningglory                                                                           2C    9G    9C    9G    0     0     1C,9G 0                            Cocklebur                                                                              --    10E   9H    9H    0     0     --    0                            Sicklepod                                                                              5G    4C,9G 4C,9G 3C,9G 0     0     2C,7G 0                            Nutsedge                                                                               0     10E   9G    10E   0     0     2C,7G 0                            Crabgrass                                                                              0     4G,2C 2C,5G 3C,9G 1C    0     1C    0                            Barnyardgrass                                                                          2C,5H 5C,9H 5C,9H 9H    0     0     3C,8G 0                            Wild Oats                                                                              2C,8G 4C,8H 5C,9H 5C,9H 0     0     1C,7G 0                            Wheat   2C,8G 8H    3C,9H 3C,9H 2G    0     1C,7G 0                            Corn    2C,9H 4C,7G 9H    9H    2C    0     3C,9H 0                            Soybean 2G    4C,7H 8H    9H    2C    0     7H    0                            Rice    10E   10E   10E   10E   3C    3G    3C,7H 0                            Sorghum 2C,9H 4C,9G 5C,9H 2C,9H 3C    0     3C,8H 0                            __________________________________________________________________________             Compound 17 Cmpd. 18                                                                             Cmpd. 19                                                                             Cmpd. 20                                                                             Cmpd. 21                                                                             Cmpd. 22                                                                             Cmpd. 23                     Rate g/ha                                                                              50    50    50    50    50    50    400   50                           __________________________________________________________________________     POST-EMERGENCE                                                                 Bush bean                                                                              3C,9G,6Y                                                                             9C    3C,6H,6Y                                                                             5C,9G,6Y                                                                             4C,5G,6Y                                                                             4C,7G,6Y                                                                             4C,5H,6Y                                                                             2C,4C,6Y                     Cotton  0     5C,9G 0     1C    1C    2C,2H 1C    2C                           Morningglory                                                                           3C,8G 9C    0     2C,4G 2C,4G 2C,2H 2C    2C,4G                        Cocklebur                                                                              3C,8G 9C    2G    2C,9G 2C,6G 3C,8G 1C    2C,2H                        Sicklepod                                                                              1C    9C    0     2C    2C    2G    0     0                            Nutsedge                                                                               1C    2C,8G 0     0     2G    0     0     0                            Crabgrass                                                                              0     2C,8G 0     0     2G    2C,2G 2G    2C,9G                        Barnyardgrass                                                                          1C,2H 9C    1H    0     2C,7H 2C,4H 1H    5C,9H                        Wild Oats                                                                              0     2C,9G 5G    2C,8G 5C,9G 0     0     5C,7H                        Wheat   0     3C,9G 2C,5G 6G    9C    0     0     9C                           Corn    2C,7H 2U,9G 2C,9G 0     4C,9H 3C,9H 2C,4G 5G                           Soybean 5G    5C,9G 0     2C,9G 3C,9G,5X                                                                             4C,6G 0     3C,8G,8X                     Rice    6G    5C,9G 5C,9G 5C,9G 5C,9G 2C,7G 2C,5G 2C,9G                        Sorghum 4G    4C,9G 2C,8H 2C,9G 4C,9G 4C,9H 2C,5G 2C,9G                        Sugar beet                                                                             2G    5C,9G 0     4C,9G 3C,7G 4C,6G 2C    0                            PRE-EMERGENCE                                                                  Morningglory                                                                           5G     9C   0     5G    0     2G    2C    0                            Cocklebur                                                                              9H    9H    0     0     0     0     5G    0                            Sicklepod                                                                              5G    9G    0     2C,9G 0     2G    2G    0                            Nutsedge                                                                               0     10E   0     0     0     0     0     0                            Crabgrass                                                                              0     2C,8G 0     2C    0     2G    2G    2C,5G                        Barnyardgrass                                                                          2C,2H 2C,9H 0     2C,4G 0     1C    1C    2H                           Wild Oats                                                                              3G    5C,9H 0     2C,9G 0     2G    2G    2C,7G                        Wheat   0     5C,9H 0     2C,9G 0     0     2G    5C,9G                        Corn    2G    10H   0     2C,9G 1C    2C,5G 2C    1C                           Soybean 2C    9H    0     3C,3H 1C    0     0     0                            Rice    3C,5G 10E   0     10E   0     1C    2C,9H 2G                           Sorghum 0     4C,9H 0     3C,9H 2G    2C,7G 3C,7G 2C                           Sugar beet                                                                             9G    5C,9G 0     5C,9G 3H    6G    3G    3H                           __________________________________________________________________________             Cmpd. 24                                                                             Cmpd. 25                                                                             Cmpd. 26                                                                             Cmpd. 27                                                                             Cmpd. 28                                                                             Cmpd. 29                                                                             Cmpd. 30                                                                             Cmpd. 31                     Rate g/ha                                                                              50    50    50    50    50    50    50    50                           __________________________________________________________________________     POST-EMERGENCE                                                                 Bush bean                                                                              0     1C    5C,8G,6Y                                                                             --    --    --    --    --                           Cotton  0     0     1C    0     4C,6H 0     0     0                            Morningglory                                                                           0     1C,2H 3C,8G 0     3C,8G 1C    0     0                            Cocklebur                                                                              0     2C,8G 2C,9H 0     4C,9H 0     0     0                            Sicklepod                                                                              0     1C    3C    0     4C,9G 0     0     0                            Nutsedge                                                                               0     0     8G    0     2C,9G 0     0     0                            Crabgrass                                                                              0     0     2C,9G 0     3C,9G 0     0     0                            Barnyardgrass                                                                          0     0     9C    0     3C,9H 0     0     0                            Wild Oats                                                                              0     0     5C,9G 0     4C,9G 0     0     0                            Wheat   0     0     6C,9G 0     4C,9G 0     0     0                            Corn    0     0     2C,9H 0     4U,9G 0     0     0                            Soybean 0     2H    4C,8G 0     2C,8G 0     0     0                            Rice    0     0     5C,9G 0     5C,9G 0     0     0                            Sorghum 0     0     5C,9G 0     4C,9G 0     0     0                            Sugar beet                                                                             0     2C,7G 3C,6G 0     5C,9H 0     0     0                            PRE-EMERGENCE                                                                  Morningglory                                                                           0     2C    5G    0     8G    0     0     0                            Cocklebur                                                                              0     --    5H    0     2C,8H 0     0     0                            Sicklepod                                                                              0     2G    2G    0     5G    0     0     0                            Nutsedge                                                                               0     0     0     0     9G    0     0     0                            Crabgrass                                                                              0     2G    2C,4G 0     2C,6G 0     0     0                            Barnyardgrass                                                                          0     2C    4C,9H 0     5C,9H 0     0     0                            Wild Oats                                                                              0     0     2C,9G 0     3C,8H 0     0     0                            Wheat   0     0     6C,9H 0     4C,9H 0     0     0                            Corn    0     0     2C,9G 0     9G    0     0     0                            Soybean 0     0     1C,1H 0     1C    0     0     0                            Rice    0     2C    9H    0     10E   0     0     0                            Sorghum 0     2G    5C,9H 0     4C,9H 0     0     0                            Sugar beet                                                                             0     6G    8G    0     2C,8G 0     0     0                            Cotton  --    --    --    0     6G    0     0     0                            __________________________________________________________________________                   Cmpd. 32                                                                             Cmpd. 33                                                                             Cmpd. 34                                                                             Cmpd. 35                                                                             Cmpd. 36                                                                             Cmpd. 37                                                                             Cmpd. 38                     Rate g/ha     50    50    50    50    50    50    50                           __________________________________________________________________________     POST-EMERGENCE                                                                 Bush bean     --    --    --    --    --    0     0                            Cotton        5C,9G 3C,4H 4C,9G 0     0     0     0                            Morningglory  9C    1C,3G 9C    0     0     0     0                            Cocklebur     2C,9G 0     5C,9G 0     0     0     0                            Sicklepod     5C,9G 0     5C,9G 0     0     0     0                            Nutsedge      4C,9G 6G    9G    0     0     0     5G                           Crabgrass     3C,8G 2C,5H 2C,9G 0     0     0     0                            Barnyardgrass 3C,8H 2C,8G 3C,9H 0     0     0     0                            Wild Oats     4C,9G 10C   3C,9G 0     0     0     0                            Wheat         5C,9G 2U,9G 9C    0     0     0     0                            Corn          4C,9G 3C,8G 4U,9G 0     0     0     0                            Soybean       3C,9G 5C,9G 9C    0     0     0     0                            Rice          5C,9G 3C,9G 5C,9G 0     0     0     0                            Sorghum       5C,9G 2C,8G 4C,9G 0     0     0     0                            Sugar beet    9C    2C,6H 5C,9G 0     0     0     0                            PRE-EMERGENCE                                                                  Morningglory  9G    0     9G    0     0     0     0                            Cocklebur     8G    0     9H    0     0     0     0                            Sicklepod     4C,9G 0     9G    0     0     0     0                            Nutsedge      2C    0     9G    0     0     0     5G                           Crabgrass     1C    0     7G    0     0     0     0                            Barnyardgrass 2C,3G 0     2C,7H 0     0     0     0                            Wild Oats     5C,8H 1C,3G 3C,8G 0     0     0     0                            Wheat         6C,9H 5C,9H 2C,8H 0     0     0     0                            Corn          5C,9H 8G    2C,9G 0     0     0     0                            Soybean       4C,9H 0     8H    0     0     0     0                            Rice          10E   9H    10E   0     0     0     0                            Sorghum       5C,9G 2C,5G 5C,9H 0     0     0     0                            Sugar beet    5C,9G 3H    4C,9G 0     0     0     0                            Cotton        7G    0     9G    0     0     0     0                            __________________________________________________________________________

TEST B

Two plastic bulb pans were filled with fertilized and limed Fallsington silt loam soil. One pan was planted with corn, sorghum, Kentucky bluegrass and several grass weeds. The other pan was planted with cotton, soybeans, purple nutsedge (Cyperus rotundus), and several broadleaf weeds. The following grass and broadleaf weeds were planted: crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa), velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A 12.5 cm diameter plastic pot was also filled with prepared soil and planted with rice and wheat. Another 12.5 cm pot was planted with sugar beets. The above four containers were treated pre-emergence with several test compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated and visually rated for response to the chemical treatments utilizing the rating system described previously for Test A. The data are summarized in Table B. Note that the compounds tested are highly active herbicides and retard the growth of several plant species.

                                      TABLE B                                      __________________________________________________________________________     PRE-EMERGENCE ON                                                               FALLSINGTON SILT LOAM                                                          __________________________________________________________________________             Compound 1                                                                             Compound 2                                                                             Compound 3                                                                             Compound 5                                                                             Compound 6                                                                             Compound 7                     Rate kg/ha                                                                             .03 .120                                                                               .03 .120                                                                               .03 .120                                                                               .03 .120                                                                               .03 .120                                                                               .03 .120                       __________________________________________________________________________     Crabgrass                                                                              5G  7G,3H                                                                              0   0   4G  6G  5G  8G,3H                                                                              7G  8G,3H                                                                              7G  8G,3H                      Barnyardgrass                                                                          6G  96,5C                                                                              0   3G  7G  8G,3C                                                                              7G,5H                                                                              10C 9G,8C                                                                              10C 9G,8C                                                                              9G,8C                      Sorghum 8G,5H                                                                              10C 5G,3H                                                                              6G,5H                                                                              6G,5H                                                                              7G,5H                                                                              --  --  --  --  --  --                         Wild Oats                                                                              6G,3H                                                                              7G,5H                                                                              0   4G  4G  6G  7G,3H                                                                              8G,6C                                                                              8G,5H                                                                              8G,3H                                                                              7G,3H                                                                              7G,3H                      Johnsongrass                                                                           8G,5H                                                                              9G,5H                                                                              0   4G  6G,3H                                                                              8G,5H                                                                              9G,8C                                                                              9G,8C                                                                              8G,3H                                                                              7G,3C                                                                              8G,5H                                                                              8G,8C                      Dallisgrass                                                                            3G  8G,3H                                                                              0   2G  2G  5G  8G  9G,8C                                                                              9G,8C                                                                              9G,8C                                                                              9G,8C                                                                              9G,7C                      Giant foxtail                                                                          4G,3H                                                                              9G,5H                                                                              0   2G  4G,3H                                                                              6G,5H                                                                              4G,3H                                                                              9G,9C                                                                              9G,9C                                                                              9G,9C                                                                              9G,7C                                                                              9G,9C                      Ky. bluegrass                                                                          5G  7G,7C                                                                              0   0   5G  7G,5C                                                                              8G,8C                                                                              10C 10C 10C 10C 10C                        Cheatgrass                                                                             5G  10C 0   3G  0   3G  7G,8C                                                                              9G,9C                                                                              10C 8G,7C                                                                              10C 10C                        Sugar beets                                                                            7G,5C                                                                              9G,8C                                                                              0   0   6G,4C                                                                              9G,9C                                                                              7G,5H                                                                              10C 9G,9C                                                                              10C 10C 10C                        Corn    3G  5G  0   0   3G  6G,3H                                                                              6G,3H                                                                              10C 10C 10C 9G,9C                                                                              10C                        Mustard 9G,9C                                                                              10C 0   7G,3H                                                                              7G,5C                                                                              9G,9C                                                                              8G,8C                                                                              10C 10C 10C 10C 10C                        Cocklebur                                                                              5G  6G,3H                                                                              0   0   3G  5G  7G,3C                                                                              7G,5H                                                                              7G  7G,5H                                                                              7G,5H                                                                              8G,5H                      Pigweed 9G,9C                                                                              9G,9C                                                                              0   0   5G  8G,8C                                                                              8G,5C                                                                              10C 8G,8C                                                                              10E 10C 10E                        Nutsedge                                                                               0   8G  0   0   0   8G  8G  10E 8G  9G  10E 10E                        Cotton  4G  8G,5H                                                                              0   0   0   7G,5H                                                                              4G,5H                                                                              8G,5H                                                                              8G,5H                                                                              9G,5H                                                                              8G,5H                                                                              9G,5H                      Morningglory                                                                           8G,3C                                                                              8C,6C                                                                              0   3G  3G  9G,6C                                                                              7G,5H                                                                              9G,5C                                                                              9G,7C                                                                              8G,7C                                                                              9G,7C                                                                              9G,9C                      Sicklepod                                                                              8G  8G,6C                                                                              0   0   8G,3H                                                                              9G,5C                                                                              6G  9G,7C                                                                              9G,7C                                                                              9G,9C                                                                              9G,9C                                                                              9G,9C                      Teaweed 3G  7G,3C                                                                              0   0   0   5G,5H                                                                              6G  6G  6G,3H                                                                              8G,5H                                                                              7G  8G,5C                      Velvetleaf                                                                             5G,5H                                                                              9G,9C                                                                              0   0   7G,5H                                                                              9G,9C                                                                              7G,5H                                                                              8G,8C                                                                              6G,5H                                                                              9G,7C                                                                              9G,7C                                                                              9G,9C                      Jimsonweed                                                                             3G  9G,9C                                                                              0   0   4G  8G,5C                                                                              5G  8G,8C                                                                              8G,8C                                                                              9G,9C                                                                              10C 9G,8C                      Soybean 0   8G,5H                                                                              0   0   0   3G,2H                                                                              6G,5H                                                                              9G,5H                                                                              9G,5H                                                                              9G,5H                                                                              9G,5H                                                                              9G,9C                      Rice    10C 10E 4G  3G,2H                                                                              6G,3H                                                                              10E 10E 10E 10E 10E 10E 10E                        Wheat   3G  6G  0   0   0   3G  5G  9G,9C                                                                              8G,7C                                                                              10C 5G  9G,9C                      __________________________________________________________________________                              Compound 9                                                                            Compound 10                                                                            Compound 11                                                                            Compound 12                                     Rate kg/ha                                                                             .03                                                                               .120                                                                               .03 .120                                                                               .03 .120                                                                               .03 .120                       __________________________________________________________________________                      Crabgrass                                                                              0  0   0   2G  0   6G  3G  4G                                          Barnyardgrass                                                                          0  0   4G  9G,3H                                                                              9G,3H                                                                              9G,9C                                                                              9G,5H                                                                              9G,9C                                       Sorghum 0  5G,3H                                                                              8G,3H                                                                              9G,9C                                                                              10E 10C 10E 10E                                         Wild Oats                                                                              2G 3G  7G  8G  8G  8G,3C                                                                              7G  7G,3C                                       Johnsongrass                                                                           0  0   8G,3H                                                                              10C 8G,3H                                                                              8G,3H                                                                              8G,4C                                                                              8G,8C                                       Dallisgrass                                                                            0  2G  0   8G,3H                                                                              6G  8G,3H                                                                              6G  8G                                          Giant foxtail                                                                          0  2G  0   5G  6G,3H                                                                              9G,5H                                                                              8G,5H                                                                              9G,8C                                       Ky. bluegrass                                                                          2G 5G  0   7G,5H                                                                              8G,8C                                                                              10C 8G,8C                                                                              10C                                         Cheatgrass                                                                             4G 2G  6G  8G,8C                                                                              8G,8C                                                                              9G,9C                                                                              10E 10E                                         Sugar beets                                                                            2G 4G  5G,3H                                                                              10C 9G,8C                                                                              10C 10C 10C                                         Corn    5G 5G  2G  5G,2H                                                                              5G,2H                                                                              10C 7G,5H                                                                              9G,9C                                       Mustard 3G 4G  7G,3H                                                                              9G,9C                                                                              10C 10C 9G,9C                                                                              10C                                         Cocklebur                                                                              0  0   0   9G,9C                                                                              8G,3H                                                                              8G,8C                                                                              8G,8C                                                                              9G,9C                                       Pigweed -- --  8G,8C                                                                              10C 10E 10E 9G,9C                                                                              10C                                         Nutsedge                                                                               0  4G  6G  10E 9G  9G  10E 10E                                         Cotton  0  2G  0   6G,5H                                                                              6G,3H                                                                              7G,5H                                                                              7G,5H                                                                              8G,3H                                       Morningglory                                                                           0  0   3G,3H                                                                              6G,5H                                                                              9G,7C                                                                              9G,8C                                                                              9G,8C                                                                              9G,9C                                       Sicklepod                                                                              0  4G  3G  6G  7G  9G,9C                                                                              8G,4C                                                                              9G,7C                                       Teaweed 2G 2G  3G  6G,3H                                                                              5G  8G,3H                                                                              7G  8G,3H                                       Velvetleaf                                                                             0  2G  --  8G,7C                                                                              7G,5H                                                                              9G,9C                                                                              9G,9C                                                                              10C                                         Jimsonweed                                                                             0  0   0   8G,7C                                                                              8G,5C                                                                              9G,7C                                                                              8G,5C                                                                              9G,7C                                       Soybean 0  0   0   4G,2H                                                                              4G,3H                                                                              7G,5H                                                                              8G,5H                                                                              9G,5H                                       Rice    5G 10C 8G,5H                                                                              10E 10E 10E 10E 10E                                         Wheat   0  0   0   4G  3G  7G  5G  7G                         __________________________________________________________________________ 

What is claimed is:
 1. A compound of the formula: ##STR140## where R is H or CH₃ ;Q is ##STR141## R₁ is H. C₁ -C₈ alkyl. C₃ -C₆ alkenyl, C₅ -C₆ cycloalkyl, C₅ -C₆ cycloalkenyl, C₃ -C₆ alkynyl, C₄ -C₇ cycloalkylalkyl, (R₁₇ CH)_(n) C(O)R₁₆, (R₁₇ CH)_(n) CO₂ R₁₈, (R₁₇ CH)_(n) COSR₁₉, (R₁₇ CH)_(n) CONR₂₀ R₂₁, (R₁₇ CH)_(n) SO₂ NR₂₀ R₂₁, (R₁₇ CH)_(n) SO₂ R₂₂, ##STR142## or C₁ -C₆ alkyl substituted either with (a) 1-3 atoms of F, Br or Cl; or(b) OR₁₆ ;provided that, (1) the total number of carbon atoms in R₁ is less than or equal to 8; and (2) if R₁ is other than C₁ -C₃ alkyl, then R₃ must be H; R₂, R₃ and R₄ are independently H or CH₃ ; R₅ is H, C₁ -C₄ alkyl, --OR₆, NO₂, F, Cl, Br, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ; R₆ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl C₃ -C₄ alkynyl, CO₂ R₁₈, SO₂ NR₂₀ R₂₁, SO₂ R₂₂ or C₁ -C₄ alkyl substituted with (a) 1-3 atoms of F, Cl or Br; or (b) OCH₃ ; provided that, (1) when R₅ is other than H, CH₃, OCH₃, or NO₂, then R₆ is H or CH₃ ; and (2) when R₆ is CO₂ R₁₈, SO₂ NR₂₀ R₂₁ or SO₂ R₂₂, then R₅ is H, CH₃, OCH₃ or NO₂ ; R₇ is H or CH₃ ; R₈ is H, C₁ -C₄ alkyl, --OR₁₆, NO₂, F, Cl, Br, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ; R₉ is CH₃ or C₂ H₅ ; R₁₀ is H, C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CO₂ R₂₄, SO₂ NR₂₀ R₂₁ or SO₂ R₂₂ ; R₁₁ is H, C₁ -C₃ alkyl, F, Cl, Br, NO₂, --OR₁₆, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ; provided that, when R₁₀ is other than C₁ -C₃ alkyl, then R₁₁ is H, Cl, OCH₃, NO₂ or CH₃ ;R₁₂ is H or CH₃ ; R₁₃ and R₁₄ are independently H, C₁ -C₃ alkyl --OR₁₆, F, Cl, Br, NO₂, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁ ; provided that, when either of R₁₃ or R₁₄ is CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁, then the other is H, Cl, CH₃, OCH₃ or NO₂ ; R₁₅ is H or CH₃ ; R₁₆ is C₁ -C₃ alkyl; R₁₇ is H or CH₃ ; R₁₈ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl, CH₂ CH₂ Cl or CH₂ CH₂ OCH₃ ; R₁₉ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl, C₃ -C₄ alkynyl or CH₂ CH₂ OCH₃ ; R₂₀ and R₂₁ are independently CH₃ or C₂ H₅ ; R₂₂ is C₁ -C₃ alkyl or CF₃ ; R₂₃ is H, Cl, Br, CH₃, F, CF₃, OCH₃ or NO₂ ; R₂₄ is C₁ -C₃ alkyl or allyl; R₂₅ is C₁ -C₃ alkyl; m is 0, 1 or 2; n is 0 or 1; A is R1 ? ##STR143## X is CH₃, OCH₃, OCF₂ H or SCF₂ H; Y is CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, CH(OCH₃)₂, OCH₂ CF₃, OCF₃, NH₂, NHCH₃, N(CH₃)₂ or GCF₂ T where G is O or S and T is H, CHClF, CHBrF, CF₂ H or CHFCF₃ ; Z is N; and agriculturally suitable salts thereof.
 2. A compound of claim 1 whereX is CH₃, or OCH₃ ; Y is CH₃, C₂ H₅, OCH₃, OC₂ H₅, CH₂ OCH₃, CH(OCH₃)₂, NH₂, NHCH₃ or N(CH₃)₂.
 3. Compounds of claim 1 where Q is ##STR144##
 4. Compounds of claim 3 where R is H.
 5. Compounds of claim 4 where A is ##STR145##
 6. Compounds of claim 5 where X is CH₃, OCH₃ or OCF₂ H and Y is CH₃ ; OCH₃ or OCF₂ H.
 7. Compounds of claim 6 where R₁ is H or C₁ -C₄ alkyl, and R₃ is H.
 8. Compounds of claim 1 where Q is ##STR146##
 9. Compounds of claim 8 where R is H.
 10. Compounds of claim 9 where A is ##STR147## and R₄ is H.
 11. Compounds of claim 10 where X is CH₃, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.
 12. Compounds of claim 11 where R₅ is H, CH₃, OCH₃, Cl, NO₂, CO₂ R₂₄ or SO₂ NR₂₀ R₂₁ and R₆ is H or C₁ -C₄ alkyl.
 13. Compounds of claim 1 where Q is ##STR148##
 14. Compounds of claim 13 where R is H.
 15. Compounds of claim 14 where A is ##STR149## and R₇ is H.
 16. Compounds of claim 15 where X is CH₃, OCH₃, or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.
 17. Compounds of claim 16 where R₈ is Br, C₁ -C₄ alkyl, OCH₃, Cl, NO₂, CO₂ R₂₄, S(O)_(m) R₂₅ or SO₂ NR₂₀ R₂₁.
 18. Compounds of claim 1 where Q is ##STR150##
 19. Compounds of claim 18 where R is H.
 20. Compounds of claim 19 where A is ##STR151##
 21. Compounds of claim 20 where X is CH₃, OCH₃, or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.
 22. Compounds of claim 1 where Q is ##STR152##
 23. Compounds of claim 22 where R is H.
 24. Compounds of claim 23 where A is ##STR153##
 25. Compounds of claim 24 where X is CH₃, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.
 26. Compounds of claim 25 where R₁ is H, CH₃, OCH₃, Cl, Br, NO₂, CO₂ CH₃, SO₂ CH₃ or SO₂ N(CH₃)₂.
 27. Compounds of claim 1 where Q is ##STR154##
 28. Compounds of claim 27 where R is H.
 29. Compounds of claim 28 where A is ##STR155##
 30. Compounds of claim 29 where X is CH₃, OCH₃ or OCF₂ H and Y is CH₃, OCH₃ or OCF₂ H.
 31. A compound of claim 1 which is 5-[[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]aminosulfonyl]-1-methyl-1H-pyrazole-4-carboxylic acid, methyl ester.
 32. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 1 and at least one of the following: surfactant, solid or liquid diluent.
 33. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 2 and at least one of the following: surfactant, solid or liquid diluent.
 34. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 3 and at least one of the following: surfactant, solid or liquid diluent.
 35. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 4 and at least one of the following: surfactant, solid or liquid diluent.
 36. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 5 and at least one of the following: surfactant, solid or liquid diluent.
 37. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 6 and at least one of the following: surfactant, solid or liquid diluent.
 38. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 7 and at least one of the following: surfactant, solid or liquid diluent.
 39. A composition suitable for controlling the growth of undesured vegetation comprising an effective amount of a compound of claim 8 and at least one of the following: surfactant, solid or liquid diluent.
 40. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 9 and at least one of the following: surfactant, solid or liquid diluent.
 41. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 10 and at least one of the following: surfactant, solid or liquid diluent.
 42. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 11 and at least one of the following: surfactant, solid or liquid diluent.
 43. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of a compound of claim 12 and at least one of the following: surfactant, solid or liquid diluent.
 44. A composition suitable for controlling the growth of undesired vegetation comprising an effective amount of the compound of claim 31 and at least one of the following: surfactant, solid or liquid diluent.
 45. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 1. 46. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 2. 47. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 3. 48. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 4. 49. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 5. 50. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 6. 51. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 7. 52. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 8. 53. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 9. 54. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 10. 55. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 11. 56. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of a compound of claim
 12. 57. A method for controlling the growth of undesired vegetation which comprises applying to the locus to be protected an effective amount of the compound of claim
 31. 